Title: Top 10 Hotels in Sheffield, MA (from $74) 2026 - Competitive Prices | Expedia.com [Sheffield Travel Guide](https://expedia.com/Sheffield.dx157238)[Vacation Rentals in Sheffield](https://expedia.com/Sheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Flights to Sheffield](https://expedia.com/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Car Rentals in Sheffield](https://expedia.com/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)[Sheffield Vacation Packages](https://expedia.com/Sheffield.d157238.Destination-Travel-Guides) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Go beyond your typical stay in Sheffield Pool [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&amenities=POOL) Pet-friendly [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&amenities=PETS) Great for families [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&travelerType=family_friendly) Cabins [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&lodging=CABIN) Farm [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&lodging=AGRITOURISM) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&amenities=HOT_TUB) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-03-11&d1=2026-03-11&endDate=2026-03-13&d2=2026-03-13&lodging=COTTAGE) ## Check prices for these dates Tonight [Feb 25 - Feb 26](https://www.expedia.com/Hotel-Search?regionId=157238&startDate=2026-02-25&endDate=2026-02-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 26 - Feb 27](https://www.expedia.com/Hotel-Search?regionId=157238&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=157238&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=157238&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield hotels ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/143186d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f060dba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/0603c149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilder House Berkshires [](https://www.expedia.com/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) Sheffield 9.8/10 Exceptional (43 reviews) "Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristinna $184 nightly $206 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Premium bedding, down comforters, pillowtop beds, individually furnished](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (19 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary $139 nightly $155 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) Great Barrington 8.8/10 Excellent (739 reviews) "Great property, very accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shanice $103 nightly $115 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (824 reviews) "The room was clean, and the staff was friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damien $67 nightly $74 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/c24971a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/0f74ae3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee - Lenox South [](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) Lee 8.4/10 Very Good (1,005 reviews) "Safe, clean rooms, decent breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil $87 nightly $97 total Mar 25 - Mar 26 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (834 reviews) "Clean room and the bed was very comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arlan $69 nightly $77 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/30ceb892.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/04ff4b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locust Tree Bed and Breakfast LLC [](https://www.expedia.com/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information) East Canaan 9.0/10 Wonderful (415 reviews) "Great breakfast! Had a wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle $105 nightly $121 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/390a52f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Valley Motel West Stockbridge [](https://www.expedia.com/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) West Stockbridge 6.8/10 (1,001 reviews) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne $59 nightly $64 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking, No Children Allowed | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,017 reviews) "Very friendly staff comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle $93 nightly $103 total Mar 5 - Mar 6 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/ecdcd2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; Mediterranean cuisine ](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/5fe2b5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/cefd2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (5) | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/110000000/109830000/109821100/109821051/6375a3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Millerton Inn [](https://www.expedia.com/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) Millerton 8.2/10 Very Good (16 reviews) "Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie $161 nightly $182 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Millerton-Hotels-The-Millerton-Inn.h109821051.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (864 reviews) "This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa $119 nightly $133 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking | In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (572 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad $75 nightly $84 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (83 reviews) "it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura Pearson $132 nightly $147 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1,000 reviews) "Clean room, nice staff , decent breakfast. Overall a good stay . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anindita $98 nightly $109 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking | 1 bedroom, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/f25ff27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking | Bathroom | Combined shower/tub, deep soaking tub, hydromassage showerhead](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/591bd0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Great Barrington [](https://www.expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) Great Barrington 8.4/10 Very Good (1,001 reviews) "Clean room, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea $66 nightly $74 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (863 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick $142 nightly $158 total Mar 27 - Mar 28 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed) | 1 bedroom](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (446 reviews) "Had everything we needed. Very thoughtful touches. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark $95 nightly $105 total Mar 3 - Mar 4 Total with taxes and fees [](https://www.expedia.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/279dc540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (554 reviews) "Great friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo $110 nightly $123 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![50-inch flat-screen TV with digital channels, Netflix, toys](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/17c4dc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/63dfffc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/9885d0cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, Roll-in Shower | Individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125350000/125340300/125340225/7d38f095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Berkshire Mountain Inn [](https://www.expedia.com/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information) Great Barrington $200 nightly $223 total Feb 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-The-Berkshire-Mountain-Inn.h125340225.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room, 2 Queen Beds, Courtyard View | Premium bedding, pillowtop beds, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.com/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Great Barrington 9.6/10 Exceptional (38 reviews) "The room was clean and comfortable wi will back next year:) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadya $123 nightly $138 total Mar 20 - Mar 21 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-11&endDate=2026-03-12®ionId=157238&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=HTG_SPRING_PROMO_157238) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Hotels.d157238.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Hotels.d157238.Travel-Guide-Hotels) ## Stay near popular Sheffield attractions ### Magnolia Bluffs Casino Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532644877) ### Drury Preserve Explore diverse ecosystems along a serene 2.4-mile trail through hemlock forests and calcareous wetlands. Cross wooden boardwalks to a tranquil pond where great blue herons and other wildlife await. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909393154894376960) ### Ashley House Built in 1735, the Ashley House is where Elizabeth Freeman successfully sued for her freedom, helping end slavery in Massachusetts. Tour the historic rooms and learn about this pivotal chapter in American history. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532664810) ### Lime Kiln Farm Wildlife Sanctuary This wildlife sanctuary showcases diverse plant species across limestone ridges and conifer forests. Explore trails to spot numerous butterfly species and Pileated Woodpeckers in the tranquil Berkshires landscape. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909392771425624064) ### Bartholomews Cobble Twin rocky knolls form this National Natural Landmark, home to one of North America's most diverse fern collections. Explore five miles of trails through forests and riverbanks for exceptional wildlife viewing. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909390447198502912) ### Bartholomew's Cobble This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909390908452102144) ### Thom Reed UFO Monument Park America's first officially documented UFO encounter is commemorated at this riverside park in Sheffield. Explore plaques about the Reed family's 1969 experience while enjoying Housatonic River views. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=858298811991220224) ## Learn more about Sheffield Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green. [See all hotels in Sheffield](https://www.expedia.com/Hotel-Search?startDate=2026-03-11&endDate=2026-03-12&adults=2®ionId=157238) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Sheffield Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Room was spotless! Kitchen was so helpful. Pool was a major hit with the kids and was warm even though it was February! They spent hours in the pool and outdoor hot tub. Will definitely stay here again!" [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Nice and responsive" [](https://expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Affordable price, clean bedroom and close to everything. " [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean, breakfast was a nice option before heading to Butternut mountain nearby " [](https://expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg) ### The Whitlock 10/10 Excellent "Lovely historical hotel within walking distance to many great shops and restaurants. Staff members maintained good communication and were very helpful throughout our stay. Rooms were clean, quiet, and comfortable. Would definitely stay there again." [](https://expedia.com/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Beautiful room with a fireplace. " [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "convenient location, wonderful breakfast, very clean and comfortable" [](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "great customer service" [](https://expedia.com/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Really cute spaces. Comfy beds and great location." [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ## More cheap stays in Sheffield ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 372 Main Street Great Barrington MA $66 nightly $74 total Mar 23 - Mar 24 Total with taxes and fees 8.4/10 Very Good! (1,001 reviews) [](https://expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Monument Mountain Motel 247 Stockbridge Rd Great Barrington MA $67 nightly $74 total Feb 26 - Feb 27 Total with taxes and fees 9/10 Wonderful! (824 reviews) [](https://expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA $69 nightly $77 total Feb 26 - Feb 27 Total with taxes and fees 7.6/10 Good! (834 reviews) [](https://expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street Lee MA $87 nightly $97 total Mar 25 - Mar 26 Total with taxes and fees 8.4/10 Very Good! (1,005 reviews) [](https://expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA $93 nightly $103 total Mar 5 - Mar 6 Total with taxes and fees 9.2/10 Wonderful! (1,017 reviews) [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 415 Stockbridge Rd Great Barrington MA $103 nightly $115 total Mar 1 - Mar 2 Total with taxes and fees 8.8/10 Excellent! (739 reviews) [](https://expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ## Hotels in Sheffield with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 1 properties [](https://expedia.com/5Star-Sheffield-Hotels.s50-0-d157238.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 13 properties [](https://expedia.com/4Star-Sheffield-Hotels.s40-0-d157238.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 120 properties [](https://expedia.com/3Star-Sheffield-Hotels.s30-0-d157238.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 103 properties [](https://expedia.com/2Star-Sheffield-Hotels.s20-0-d157238.Travel-Guide-Filter-Hotels) ## Find out more about Sheffield ### Top reasons to visit Sheffield - **Adventure Sports:** Sheffield is a haven for outdoor enthusiasts, offering excellent skiing and various sports activities. - **Scenic Nature:** Visitors can explore stunning parks, lakes, and nature reserves, perfect for eco-friendly adventures. - **Charming Accommodations:** Enjoy a range of lodging options, from cozy bed & breakfasts to unique agritourism stays. - **Rich Historical Atmosphere:** Sheffield's charming vibe and friendly locals create a memorable vacation experience. - **Relaxation Opportunities:** Unwind at local spas and enjoy leisure activities amidst beautiful natural surroundings. ### Find great hotels near Sheffield Discover a charming selection of accommodations in Sheffield, Massachusetts, perfect for every type of traveler. From cozy bed & breakfasts to unique agritourism properties, Sheffield offers pet-friendly options and family-friendly facilities for an unforgettable adventure vacation experience. Explore the best hotels, read reviews, and find the perfect lodging to suit your needs while enjoying the beautiful surroundings of the Berkshires. - **[Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: ](https://www.expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)** Nestled in the heart of the Berkshires, this 3.5-star resort offers a perfect blend of adventure and family-friendly amenities. With a focus on outdoor activities, guests can enjoy easy access to ski lifts, snowboarding, and hiking trails nearby. The resort is designed for families, featuring a mini-golf course, arcade game room, and a playground for children. Whether you’re hitting the slopes or relaxing with loved ones, this resort promises a fun-filled experience for guests of all ages. - **[Quality Inn: ](https://www.expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)** Located just 6 miles from Sheffield, Quality Inn is ideal for those combining business and adventure. This property caters to business travelers with essential amenities such as meeting rooms and a business center. For the adventure-seekers, nearby activities include snowshoeing, downhill skiing, and snowboarding, making it an excellent choice for those wanting to mix work with play. The welcoming atmosphere and convenient location make it an attractive option for both professionals and leisure travelers. - **[Holiday Inn Express Hotel & Suites Great Barrington by IHG: ](https://www.expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)** Just 7 miles from Sheffield, this hotel stands out as a welcoming space for business and LGBTQIA travelers. With 24-hour business center access and conference facilities, it’s perfect for meetings and corporate events. Guests appreciate the inclusive environment, making it a comfortable retreat. The hotel’s modern amenities, combined with a commitment to hospitality, ensure a pleasant stay for anyone visiting the area, whether for work or leisure. ### Where to stay near Sheffield Sheffield, Massachusetts, offers an ideal getaway for tourists seeking adventure and relaxation. With its charming historical vibe, you'll find an array of family-friendly activities and stunning scenery. Nearby cities and neighborhoods provide a romantic atmosphere and friendly locals, making it perfect for a memorable vacation. Explore Sheffield's ski resorts and outdoor sports, and don't miss out on exciting vacation packages that highlight the best places to visit within walking distance. Your adventure awaits. - **[Great Barrington: ](https://www.expedia.com/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)** Located 6 miles from Sheffield, Great Barrington is a charming city that attracts visitors year-round, particularly during the summer months from June to August. Known for its outdoor adventure offerings, this inviting destination is popular for skiing and sports enthusiasts. Visitors can enjoy the nearby ski fields and resorts, making it a perfect spot for thrill-seekers. The area's natural beauty includes serene lakes and majestic mountains, complemented by the stunning landscapes of the national state park. Great Barrington is an ideal base for adventure lovers looking to immerse themselves in the great outdoors. - **[The Berkshires: ](https://www.expedia.com/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)** Situated 11 miles from Sheffield, The Berkshires is famed for its breathtaking scenery and outdoor activities. This region experiences steady visitor traffic throughout the year, with peaks in the summer months from June to August. Renowned for its skiing opportunities, The Berkshires offers a wealth of adventure for nature lovers. In addition to ski resorts, visitors can explore beautiful lakes and mountains, providing a perfect backdrop for hiking, fishing, or simply enjoying the picturesque views. The event conference venues also make it a great location for cultural experiences and gatherings. - **[Ashley Falls: ](https://www.expedia.com/Ashley-Falls-Hotels.d901768766462177280.Travel-Guide-Hotels)** Just 4 miles from Sheffield, Ashley Falls is a quaint city that sees moderate seasonal traffic, peaking during the summer and fall months. Visitors are drawn here for its exciting ski and sports offerings, along with a variety of adventure experiences. The nearby ski fields and resorts cater to winter sports enthusiasts, while the local parks and town hall enhance the community's charm. Ashley Falls blends adventure with small-town hospitality, making it a delightful stop for travelers looking to enjoy both outdoor activities and a warm, welcoming atmosphere. ### Things to do near Sheffield Sheffield, Massachusetts, is perfect for adventure seekers and sports enthusiasts, offering fantastic skiing opportunities at local ski resorts and fields. Visitors can explore numerous parks for outdoor activities and unwind at a spa show for relaxation. With its blend of recreation and leisure, Sheffield promises an exciting vacation experience for everyone. **Shopping** In Sheffield, you'll find local charm at shops like [Hoffman's Pottery](https://www.expedia.com/Hoffmans-Pottery-Hotels.0-l553248621532665251-0.Travel-Guide-Filter-Hotels). If you're up for a drive, [Lee Premium Outlets](https://www.expedia.com/Lee-Premium-Outlets-Hotels.0-l6127084-0.Travel-Guide-Filter-Hotels) and [Berkshire Mountain Country Store](https://www.expedia.com/Berkshire-Mountain-Country-Store-Hotels.0-l553248621532665264-0.Travel-Guide-Filter-Hotels), both 14 and 15 miles away respectively, offer a wider selection of gifts and souvenirs in a vibrant shopping atmosphere. **Recreation** Experience tranquility at [Lake Mansfield Park](https://www.expedia.com/Lake-Mansfield-Park-Hotels.0-l553248621560926695-0.Travel-Guide-Filter-Hotels), where you can unwind in nature and enjoy serene walks around the lake. For music lovers, [Music Mountain](https://www.expedia.com/Music-Mountain-Hotels.0-l553248621561735303-0.Travel-Guide-Filter-Hotels) offers delightful concerts in a picturesque setting. If you're in the mood for sports, the [Greenock Country Club](https://www.expedia.com/Greenock-Country-Club-Hotels.0-l553248621560926703-0.Travel-Guide-Filter-Hotels) provides a beautiful golf course for outdoor recreation. **Adventure** At [Ski Butternut](https://www.expedia.com/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels), located 5 miles from Sheffield, enjoy thrilling skiing experiences with vibrant sports energy. The [Housatonic River Walk](https://www.expedia.com/Housatonic-River-Walk-Hotels.0-l553248621532665241-0.Travel-Guide-Filter-Hotels), 6 miles away, offers scenic hiking adventures amidst beautiful outdoor landscapes. For a unique challenge, try the [Catamount Aerial Adventure Park](https://www.expedia.com/Catamount-Aerial-Adventure-Park-Hotels.0-l553248621532664791-0.Travel-Guide-Filter-Hotels), situated 8 miles from Sheffield, featuring exciting zipline courses. **Nightlife** Experience the vibrant nightlife in Sheffield by catching a show at the nearby [Mahaiwe Performing Arts Center](https://www.expedia.com/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels) or enjoy a delightful evening at [Infinity Music Hall and Bistro](https://www.expedia.com/Infinity-Music-Hall-And-Bistro-Hotels.0-l553248621532664806-0.Travel-Guide-Filter-Hotels). For a touch of tradition, don’t miss the [Berkshire Theatre Festival](https://www.expedia.com/Berkshire-Theatre-Festival-Hotels.0-l553248621532665249-0.Travel-Guide-Filter-Hotels), all offering a blend of culture and family-friendly entertainment. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Sheffield To save money on your trip to Sheffield, visit during the off-peak months of January and March to April for lower lodging prices. Tuesdays are the most affordable days to stay, while Saturdays are the priciest. Use Expedia to compare hotel rates and book package deals that combine flights and activities for additional savings. Consider eco-certified hotels for budget-friendly options. Joining Expedia's One Key membership can provide exclusive discounts and allow you to earn rewards for future bookings. Walking is also a great way to explore Sheffield without spending on transportation. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to narrow down your options based on your preferences, such as budget, desired location, and hotel type. For instance, selecting the Eco-certified filter will show you sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your Sheffield hotel reservation with your flights and activities through an Expedia package deal. - **Become a One Key member:** Join [Expedia's One Key membership](https://www.expedia.com/welcome-one-key) program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels. ### Find the best attractions near Sheffield Sheffield, Massachusetts, is perfect for outdoor enthusiasts seeking ski adventures, sports vacations, and eco-friendly experiences. Explore local attractions like national parks, nature reserves, and beautiful lakes, ideal for adventure seekers. If you're looking for accommodations, consider hotels near Sheffield Botanical Gardens for a relaxing stay amidst nature. - **[Taconic State Park: ](https://www.expedia.com/Taconic-State-Park-Hotels.0-l553248621532664790-0.Travel-Guide-Filter-Hotels)** Located 8 miles from Sheffield, this national park offers breathtaking scenery and a wealth of outdoor adventure opportunities. Hike through lush trails, enjoy stunning vistas, and experience the tranquility of nature in a pristine setting. - **[Housatonic River: ](https://www.expedia.com/Housatonic-River-Hotels.0-l682155708745285632-0.Travel-Guide-Filter-Hotels)** Just 6 miles away, the Housatonic River provides beautiful views and a serene atmosphere perfect for kayaking, fishing, or simply relaxing by the water. Its lush banks are ideal for picnicking and enjoying the great outdoors. - **[Umpachene Falls Park: ](https://www.expedia.com/Umpachene-Falls-Park-Hotels.0-l553248621560926710-0.Travel-Guide-Filter-Hotels)** Only 4 miles from Sheffield, this enchanting waterfall park is perfect for outdoor enthusiasts. Its romantic vibes make it a great spot for couples, while the adventurous trails invite exploration amid stunning natural beauty. ### Best time to go to Sheffield The best time to visit Sheffield is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 23.2°F (-4.9°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 24.8°F (-4.0°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | March | 32.5°F (0.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 44.2°F (6.8°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | May | 55.9°F (13.3°C) | Light Rain | Mostly Sunny | Average | Average | | June | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 69.8°F (21.0°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 60.8°F (16.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 49.8°F (9.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 37.8°F (3.2°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | ### The nearest major airports for your trip to Sheffield When planning your trip to Sheffield, Massachusetts, there are several major airports to consider. Hartford, CT ([BDL](https://www.expedia.com/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)\-Bradley Intl.) is located 37 miles away, with nearby hotels like the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.com/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1 mile from the airport. Albany, NY ([ALB](https://www.expedia.com/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)\-Albany Intl.) is 50 miles away, offering options such as the [Park Manor Hotel](https://www.expedia.com/Clifton-Park-Hotels-Park-Manor-Hotel.h895584.Hotel-Information), 8 miles from the airport. Lastly, Newburgh, NY ([SWF](https://www.expedia.com/Stewart-Intl-Airport-Hotels.0-aSWF-0.Travel-Guide-Filter-Hotels)\-Stewart Intl.) is 57 miles from Sheffield, with accommodations like [The Dutchess Inn and Spa at Beacon](https://www.expedia.com/Newburgh-Hotels-The-Dutchess-Inn-And-Spa-At-Beacon.h18730652.Hotel-Information), 6 miles from the airport. Each airport provides convenient access to these hotels and the surrounding areas. ## Frequently asked questions ### What is the best area to stay in Sheffield? > This area provides a convenient base with a selection of inns and guesthouses. Main Street is where you'll find local shops, restaurants, and art galleries, making it easy to explore the town on foot. It's also well-situated for exploring the surrounding Berkshire Hills. > > > Couples looking for a peaceful retreat will appreciate the options just outside the immediate town center. These accommodations often offer a more secluded setting with views of the natural landscape, while still being a short drive from Sheffield's amenities and nearby attractions like the Berkshire Botanical Garden. > > > For solo travelers, staying near Main Street offers the convenience of easily accessing local dining and shops. ### What are the best hotels in Sheffield that travelers recommend? > The Wilder House Berkshires, with an outstanding 9.8 rating, offers guests comfortable and clean rooms with premium bedding and air conditioning. Guests consistently praise the great and delicious free cooked breakfast, and complimentary self-parking is also available, adding to the convenience of your stay. ### What are the best family hotels in Sheffield? > This highly-rated property, with a 9.8 review score, offers a comfortable and clean stay for families. Guests frequently praise the great and delicious breakfast, and the hotel provides several complimentary amenities that are beneficial for family travel, including a free crib, free breakfast, free cooked breakfast, free self-parking, free toiletries, and free WiFi. ### What hotels in Sheffield offer free breakfast? > The Wilder House Berkshires, with an outstanding 9.8 rating, provides a highly-rated experience. Guests frequently praise the comfortable and clean rooms, as well as the great and delicious breakfast, which includes a cooked option. This hotel also offers free self-parking, free toiletries, and free WiFi, ensuring a convenient stay. It is located approximately 6.4 miles from the Housatonic River. ### What are the best budget hotels in Sheffield? > This hotel, with an outstanding 9.8 review rating, offers a comfortable and clean stay with several complimentary amenities. Guests particularly appreciate the free self-parking, free toiletries, and a delicious free cooked breakfast. Additionally, the hotel provides free WiFi and air conditioning for a pleasant stay. It's located within 6.4 miles of the Housatonic River. View all [budget hotels in Sheffield](https://www.expedia.com/Sheffield-Hotels-Cheap-Hotels.0-0-d157238-tCheapHotels.Travel-Guide-Filter-Hotels) ### When is the best time to go to Sheffield? > Autumn transforms the Berkshire landscape with vibrant colors, making it ideal for scenic drives and exploring the charming small towns. The weather is generally crisp and comfortable, superb for hiking or visiting local farms and orchards. This season is particularly appealing to couples looking for a picturesque and romantic getaway. > > > Summer offers warm temperatures and a full calendar of outdoor events and festivals. It's an excellent time for activities like kayaking on the Housatonic River, cycling on country roads, or exploring the numerous art galleries and studios in the area. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Sheffield hotel booking with Expedia? > \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo. ### How much is the nightly rate at a Sheffield hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Magnolia Bluffs Casino ](https://www.expedia.com/Magnolia-Bluffs-Casino-Hotels.0-l553248621532644877-0.Travel-Guide-Filter-Hotels) - [Hotels near Ashley House ](https://www.expedia.com/Ashley-House-Hotels.0-l553248621532664810-0.Travel-Guide-Filter-Hotels) - [Hotels near Umpachene Falls Park ](https://www.expedia.com/Umpachene-Falls-Park-Hotels.0-l553248621560926710-0.Travel-Guide-Filter-Hotels) - [Mill River Hotels ](https://www.expedia.com/Mill-River-Hotels.d3000748895.Travel-Guide-Hotels) - [South Egremont Hotels ](https://www.expedia.com/South-Egremont-Hotels.d183341.Travel-Guide-Hotels) - [Hotels near Questing ](https://www.expedia.com/Questing-Hotels.0-l553248621532664812-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Mill River ](https://www.expedia.com/5Star-Mill-River-Hotels.s50-0-d3000748895.Travel-Guide-Filter-Hotels) - [Cottages in Mill River ](https://www.expedia.com/Mill-River-Cottages.d3000748895-aaCottages.Travel-Guide-Accommodation) - [Cabin Rentals in Mill River ](https://www.expedia.com/Mill-River-Cabins.d3000748895-aaCabins.Travel-Guide-Accommodation) - [Apartments in Mill River ](https://www.expedia.com/Mill-River-Apartments.d3000748895-aaApartments.Travel-Guide-Accommodation) - [Hotels near Les Trois Emme Winery ](https://www.expedia.com/Les-Trois-Emme-Winery-Hotels.0-l553248621532664814-0.Travel-Guide-Filter-Hotels) - [Hotels near W.E.B. 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