Title: TOP 10 Hotels in Chester, MA (from $75) - COMPETITIVE PRICES | Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6005399)[Vacation Rentals in Chester](https://expedia.com/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6005399.Travel-Guide-Flights)[Car Rentals in Chester](https://expedia.com/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.com/Chester.d6005399.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Chester Family friendly [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&travelerType=family_friendly) Farm [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&lodging=AGRITOURISM) Pool [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&amenities=POOL) Pet friendly [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&amenities=PETS) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&amenities=HOT_TUB) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&lodging=APARTMENT) Cottage [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&lodging=COTTAGE) Cabin [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&lodging=CABIN) Condo [](https://www.expedia.com/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-04-13&d1=2026-04-13&endDate=2026-04-15&d2=2026-04-15&lodging=CONDO) ## Check prices for these dates Tonight [Mar 30 - Mar 31](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-30&endDate=2026-03-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 31 - Apr 1](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-03-31&endDate=2026-04-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6005399&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.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 (883 reviews) "This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Payton $78 nightly $87 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1,000 reviews) "It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristina $107 nightly $119 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.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) ### Monument Mountain Motel [](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (836 reviews) "Nice place and very reasonable for great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond $67 nightly $74 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Standard Room, 2 Queen Beds, Non Smoking | Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Kitchen (Larger Room, Sofabed, Full Kitchen) | Pillowtop beds, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/b5bac949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5754h3835x5y5-e38781aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-c074381d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baldwin Inn & Suites, SureStay Collection by Best Western [](https://www.expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) West Springfield 7.8/10 Good (154 reviews) "So close to the Big E Fairgroynds, wonderful service, would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry $101 nightly $116 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/w863h648x1y0-4d00d4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/b8e5643f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a071e69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Valley Inn [](https://www.expedia.com/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) West Hatfield 8.6/10 Excellent (127 reviews) "Friendly staff, really nice room, quiet. I really enjoyed my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desiree $99 nightly $111 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/4592453d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/d0f01d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/c682c6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Springfield Holyoke [](https://www.expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) Holyoke 9.2/10 Wonderful (624 reviews) "We enjoyed our 3 nights it was quiet and very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne $118 nightly $132 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.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) ![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 9.6/10 Exceptional (25 reviews) "Friendly staff, beautiful interiors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Izabela $139 nightly $155 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/a4915f8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/aa01ab9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mort's Library | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/f25262f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8cf443f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Naomi's Inn Bed & Breakfast [](https://www.expedia.com/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) Liberty Heights 9.0/10 Wonderful (431 reviews) "So cute and accommodating to our schedule " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carey Lynn $105 nightly $119 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/12b5137a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive King Room | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa [](https://www.expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) Holyoke 9.4/10 Exceptional (2,224 reviews) "Very clean, comfortable, and quiet hotel. We enjoyed our visit." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry $127 nightly $141 total Apr 20 - Apr 21 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.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/a831aba7.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) ![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 (1,002 reviews) "Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy $84 nightly $94 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.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) ![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) ![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) ![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 (1,002 reviews) "Great place to stay and close to shops and restaurants will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marie-Pascale $98 nightly $110 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/13980508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/07d4dc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/cb762de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/w4000h2665x0y2-3046acd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Hadley Amherst [](https://www.expedia.com/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information) Hadley 9.8/10 Exceptional (75 reviews) "The check in staff were amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) mandeep $152 nightly $170 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.2/10 Wonderful (1,002 reviews) "Room was spotless, staff was very kind!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilia $94 nightly $105 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.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) ![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 (574 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad $75 nightly $84 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/bb325877.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 (1,000 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 Mar 31 - Apr 1 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/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/ef9bad04.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/f84b737e.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 (555 reviews) "Clean … check in , good location for us .. we’ll be back in Maynn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen $110 nightly $123 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/c31a7f40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/fc5fc5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/683c1f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21300/21212/d26efba1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn West Springfield [](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.Hotel-Information) West Springfield 8.2/10 Very Good (1,003 reviews) "Very good place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gloria $106 nightly $121 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Hampton-Inn-West-Springfield.h21212.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.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 (889 reviews) "Overall pleasant stay; great facilities, staff, and location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casey $108 nightly $120 total Apr 29 - Apr 30 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/40e8ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/08190a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Chicopee Springfield [](https://www.expedia.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) Chicopee 9.0/10 Wonderful (1,001 reviews) "Best hotel in area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William $106 nightly $120 total Apr 26 - Apr 27 Total with taxes and fees [](https://www.expedia.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.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) ### 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 (87 reviews) "New hotel clean and nice. Heated pool and hot tub a bonus. Timely breakfast for early departures- great on demand coffee. Added bonus they have a car charger." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charline $118 nightly $132 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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=2026-04-13&endDate=2026-04-14®ionId=6005399&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FChester-Hotels.d6005399.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6005399.Travel-Guide-Hotels) ## Stay near popular Chester attractions ### Chester Town Hall You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## Learn more about Chester Experience the hiking, camping, and monuments in Chester! [See all hotels in Chester](https://www.expedia.com/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14&adults=2®ionId=6005399) ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=473&h=473&p=1&q=high) Photo by Chris Addams ## Top Chester Hotel Reviews ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Breakfast is excellent, quiet place is peaceful you can relax really well it has an Indian cuisine restaurant inside also a bar the restaurant is excellent all you request they will do it as long that they have it they will do everything is excellent to this In. Friendly staff." [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca_y.jpg) ### Baldwin Inn & Suites, SureStay Collection by Best Western 2/10 Terrible "We prepaid for the room. We arrived at 11PM, tired after a long drive, and they had no room. We waited a long time while the night desk clerk cleaned a room. The room wasn't very clean." [](https://expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Cute place, I would come back." [](https://expedia.com/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg) ### Fairfield Inn & Suites Springfield Northampton/Amherst 10/10 Excellent "Clean room, friendly staff and easy parking!" [](https://expedia.com/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/f05f40a5_y.jpg) ### La Quinta Inn & Suites by Wyndham Springfield MA 2/10 Terrible "Room had no hot water broken shower tile falling off They had a hockey team there on the whole floor that was partying and they were fights with cops. All four rooms did not have hot water when we showed up one of the rooms had a broken toilet." [](https://expedia.com/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "OK, the hotel needs updating, but the staff was so friendly and helpful it didn't even matter. We parked our car, walked everywhere, 2 min to the Colonial theater! Insider tip, if you buy a breakfast tix from the front desk it's less $ than paying at the restaurant. " [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "I spent 2 lovely nights here on my way through the Berkshires. Everyone was so kind, helpful and professional. Flatbread was delicious and a cup of tea in the cozy fire nook was perfect. " [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0_y.jpg) ### The Ellery 10/10 Excellent "Quaint hotel fo my stay in Northampton!" [](https://expedia.com/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg) ### Blue – A Modern Hotel, an Ascend Collection Hotel 10/10 Excellent "Jay was very helpful and informative." [](https://expedia.com/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ## More cheap stays in Chester ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/58b2bc45_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn West Springfield 1150 Riverdale St West Springfield MA $82 nightly $94 total Apr 19 - Apr 20 Total with taxes and fees 7/10 Good! (1,006 reviews) [](https://expedia.com/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Best Western Springfield West Inn](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/a76d0174_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Springfield West Inn 429 Riverdale Street West Springfield MA $93 nightly $107 total Apr 6 - Apr 7 Total with taxes and fees 7.8/10 Good! (1,005 reviews) [](https://expedia.com/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.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 $98 nightly $110 total Mar 31 - Apr 1 Total with taxes and fees 9.2/10 Wonderful! (1,002 reviews) [](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baldwin Inn & Suites, SureStay Collection by Best Western 21 Baldwin Street West Springfield MA $101 nightly $116 total Apr 6 - Apr 7 Total with taxes and fees 7.8/10 Good! (154 reviews) [](https://expedia.com/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Tru by Hilton Chicopee Springfield 440 Memorial Dr Chicopee MA $106 nightly $120 total Apr 26 - Apr 27 Total with taxes and fees 9/10 Wonderful! (1,001 reviews) [](https://expedia.com/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Blue – A Modern Hotel, an Ascend Collection Hotel 1080 Riverdale St West Springfield MA $111 nightly $128 total Apr 26 - Apr 27 Total with taxes and fees 9.6/10 Exceptional! (168 reviews) [](https://expedia.com/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ## Hotels in Chester with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 10 properties [](https://expedia.com/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 109 properties [](https://expedia.com/3Star-Chester-Hotels.s30-0-d6005399.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 58 properties [](https://expedia.com/2Star-Chester-Hotels.s20-0-d6005399.Travel-Guide-Filter-Hotels) ## Find out more about Chester ### Top reasons to visit Chester - **Outdoor Adventures:** Chester is an ideal destination for hiking, skiing, and enjoying various outdoor activities amidst its scenic landscapes. - **Charming Accommodations:** The town offers a range of cozy stays, from bed and breakfasts to comfortable hotels, catering to all types of travelers. - **Historic Sites:** Explore local history through picturesque historic houses and charming urban parks. - **Family-Friendly Atmosphere:** The town welcomes families with activities that provide fun for all ages. - **Romantic Getaways:** Chester's serene environment makes it perfect for couples seeking a romantic escape. ### Find great hotels near Chester Explore the charming town of Chester, Massachusetts, and discover a variety of hotel accommodations tailored to your needs. From cozy bed and breakfasts to comfortable hotels, you'll find options perfect for family vacations or adventurous getaways. Whether you're looking for pet-friendly options or the best hotels to enjoy a memorable stay, Chester offers a welcoming atmosphere for all travelers. - **[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)** This 3.5-star resort, with an impressive guest rating of 9.0, is a fantastic choice for those seeking a family-friendly adventure in the Berkshires. Located 15 miles from Chester, the resort offers easy access to ski lifts and shuttles, making it ideal for winter sports enthusiasts. Families will appreciate the on-site playground, arcade game room, and mini-golf, while adventure seekers can enjoy a variety of activities like skiing, snowboarding, and hiking. With its emphasis on recreation and comfort, this resort ensures a memorable stay for guests of all ages. - **[The Black Swan Lee - Lenox, an Ascend Collection Hotel: ](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)** Rated 9.2 and conveniently located 15 miles from Chester, this 3-star hotel is perfect for families and pet lovers alike. The Black Swan Lee - Lenox offers a cozy atmosphere with amenities for children, including cribs and safety features. Guests can partake in various activities such as fishing, skiing, and snow tubing. The hotel’s pet-friendly policy allows for a stress-free stay with your furry friends. Whether you're looking for a relaxing getaway or an exciting outdoor adventure, this hotel's unique charm and welcoming environment will make your visit unforgettable. - **[Quality Inn Westfield - Springfield: ](https://www.expedia.com/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information)** A budget-friendly option, the Quality Inn Westfield - Springfield is located 16 miles from Chester and offers a comfortable stay for families and business travelers. With a guest rating of 8.0, this hotel provides essential amenities such as free cribs for children and a pet-friendly policy, allowing you to bring your four-legged companions along. The hotel's convenient location offers easy access to local attractions, making it a practical choice for those seeking value and comfort on their trip. ### Where to stay near Chester Chester, Massachusetts, is a charming city perfect for outdoor adventures and romantic getaways. Explore its scenic views and historic sites while enjoying a family-friendly atmosphere. Nearby regions offer a relaxing vibe, ideal for recreation and leisurely strolls. Whether you're hiking through picturesque landscapes or indulging in local culture, Chester and its surroundings promise memories filled with charm and beauty awaiting your discovery. - **[Lenox: ](https://www.expedia.com/Lenox-Hotels.d8587.Travel-Guide-Hotels)** Nestled 17 miles from Chester, Lenox is a charming city that attracts visitors year-round, with peak travel in the summer months. Known for its rich cultural scene, Lenox offers a delightful mix of entertainment, romance, and artistic experiences. Enjoy music concerts and theatrical performances at renowned venues, or hit the nearby ski slopes in winter. The scenic beauty of the area is enhanced by picturesque lakes and mountains, making it a perfect spot for outdoor enthusiasts. Don't miss the local event conference venues that often host exciting gatherings and celebrations. - **[The Berkshires: ](https://www.expedia.com/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)** Just 12 miles from Chester, The Berkshires is a diverse region that invites adventure seekers and nature lovers alike. With a steady flow of visitors throughout the year, the area is particularly lively from June to August. Here, you can immerse yourself in outdoor activities, from skiing at top-notch resorts to exploring the stunning scenery of the mountains and lakes. The Berkshires is also home to various events and conferences, adding to its appeal as a vibrant destination for tourists seeking both excitement and relaxation. - **[Lee: ](https://www.expedia.com/Lee-Hotels.d8572.Travel-Guide-Hotels)** Located 14 miles from Chester, Lee is a delightful city that welcomes travelers with its family-friendly atmosphere and romantic charm. With a consistent influx of visitors year-round, peak seasons occur in the summer. Lee boasts a variety of entertainment options, including theaters and live music concerts, ensuring a lively experience. The area's natural beauty is complemented by historical monuments and serene lakes, providing the perfect backdrop for leisurely strolls and family outings. Whether you're seeking a cozy getaway or an action-packed adventure, Lee has something for everyone. ### Things to do in Chester Chester, Massachusetts, is perfect for outdoor adventures and romantic getaways. Visitors can enjoy skiing at local ski fields, catch a performance at the theater, or hit the golf course for a round of golf. With its scenic landscapes and charming attractions, Chester invites exploration through its various amenities and local sights, making it an ideal destination for those seeking both relaxation and adventure. **Shopping** In Chester, you can explore local shops offering unique crafts and souvenirs. If you're up for a drive, head to the nearby shopping malls like the Berkshire Mall in Lanesborough for a wider selection, or check out the Eastfield Mall in Springfield for more mainstream retailers. **Recreation** Chester's Wellness Retreat offers rejuvenating spa treatments, yoga sessions, and guided meditation in a tranquil setting. For outdoor enthusiasts, the surrounding scenic trails provide opportunities for hiking, birdwatching, and peaceful picnics, allowing you to recharge while immersing yourself in nature's beauty. **Adventure** In Chester, explore the scenic hiking trails of the Chester-Blandford State Forest, where you'll encounter breathtaking views and diverse wildlife. For water enthusiasts, the nearby Westfield River offers thrilling kayaking and canoeing experiences amidst beautiful surroundings, perfect for an adventurous day out. **Nightlife** Chester offers a charming nightlife experience with cozy bars and local eateries. Enjoy a drink at the Chester Tavern, where friendly locals gather. For a laid-back evening, try the nearby picnic spots along the river, perfect for stargazing and unwinding after a day of exploration. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Chester - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are March and December to January, 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 Chester is Tuesday. The most expensive day to stay in Chester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to narrow down your preferences, such as your budget, desired location, and type of hotel you’re looking for. 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 hotel stay in Chester with your flights and activities through an Expedia package deal. ### Find the best attractions near Chester Chester, Massachusetts, is an ideal destination for outdoor enthusiasts, adventure seekers, and couples looking for a romantic getaway. Visitors can explore a variety of attractions, including urban parks, nature reserves, and historic houses. Whether you're seeking family-friendly activities or thrilling outdoor experiences, Chester offers a delightful mix of points of interest that cater to diverse tastes and interests. - **[National Shrine of the Divine Mercy: ](https://www.expedia.com/National-Shrine-Of-The-Divine-Mercy-Hotels.0-l553248621532665250-0.Travel-Guide-Filter-Hotels)** Located 17 miles from Chester, this serene shrine offers a peaceful retreat with stunning architecture and beautiful gardens, perfect for reflection and spiritual growth. - **[Becket Land Trust Historic Quarry: ](https://www.expedia.com/Becket-Land-Trust-Historic-Quarry-Hotels.0-l553248621532666600-0.Travel-Guide-Filter-Hotels)** Just 3 miles away, this preserve combines adventure and family-friendly activities, featuring hiking trails and scenic views, making it a trendy spot for both luxury and budget travelers. - **[Littleville Lake: ](https://www.expedia.com/Littleville-Lake-Hotels.0-l553248621532666607-0.Travel-Guide-Filter-Hotels)** Located 5 miles from Chester, this picturesque lake is ideal for outdoor enthusiasts, offering opportunities for swimming, picnicking, and enjoying romantic sunset views along its scenic shoreline. ### Best time to go to Chester The best time to visit Chester 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 | 23.5°F (-4.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 25.3°F (-3.7°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | March | 33.1°F (0.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 44.8°F (7.1°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 56.5°F (13.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.4°F (18.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 70.5°F (21.4°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 68.7°F (20.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 61.9°F (16.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 50.7°F (10.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 38.8°F (3.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 30.2°F (-1.0°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Chester When traveling to Chester, Massachusetts, you have several airport options. Hartford, CT ([BDL](https://www.expedia.com/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)\-Bradley Intl.) is located 28 miles away, with nearby hotels like [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.com/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information) and [Marriott Hartford Downtown](https://www.expedia.com/Hartford-Hotels-Marriott-Hartford-Downtown.h1260819.Hotel-Information), both offering convenient access to the airport. Providence, RI ([PVD](https://www.expedia.com/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)\-T.F. Green) is 88 miles from Chester, with excellent hotel choices such as [Omni Providence Hotel](https://www.expedia.com/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Hotel Providence](https://www.expedia.com/Providence-Hotels-Hotel-Providence.h1172496.Hotel-Information) situated 7 miles from the airport. [ALB](https://www.expedia.com/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)any, NY (ALB-Albany Intl.) is 53 miles away, featuring hotels like [The Landing Hotel at Rivers Casino & Resort](https://www.expedia.com/Albany-Hotels-The-Landing-Hotel-At-Rivers-Casino-Resort.h19093277.Hotel-Information) and [DoubleTree by Hilton Schenectady Downtown](https://www.expedia.com/Albany-Hotels-DoubleTree-By-Hilton-Hotel-Schenectady.h862.Hotel-Information), both 8 miles from the airport. Each location provides accessible transportation options for travelers. ## Frequently asked questions ### What is the best area to stay in Chester? > This compact area is where you'll find the town's general store, post office, and a few local eateries. It's centered around Main Street and Middlefield Road, offering easy access to the scenic Westfield River and the start of many local hiking trails. The Chester Railway Station Museum is also a prominent feature here, providing a glimpse into the town's history. > > > For couples looking for a relaxed retreat with convenient access to outdoor activities, the village center is an excellent choice. It provides a comfortable base from which to explore the surrounding Berkshire Hills and enjoy activities like fishing, kayaking, or simply taking a scenic drive. > > > Solo travelers will also find the village center appealing due to its central location and the ease of accessing local amenities. ### When is the best time to go to Chester? > Summer offers warm, pleasant weather, ideal for exploring the outdoor attractions around Chester. You can enjoy hiking or biking on the trails of the Chester-Blandford State Forest or kayaking on the Westfield River. This period is great for active travelers and families looking to spend time outdoors without the chill of cooler seasons. > > > For those who appreciate scenic beauty and comfortable temperatures, early fall is an excellent choice. The foliage in the Berkshire Mountains surrounding Chester transforms into vibrant colors, creating stunning landscapes. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chester hotel booking with Expedia? > \*Excludes taxes and fees. 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