Title: TOP 10 Hotels in Windsor, MA (from $78) - COMPETITIVE PRICES | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6005427)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6005427.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.com/Windsor.d6005427.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 Windsor Cabin [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=CABIN) Family friendly [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&travelerType=family_friendly) Farm [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=AGRITOURISM) Pool [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=POOL) Pet friendly [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=PETS) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=APARTMENT) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=HOT_TUB) Cottage [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=COTTAGE) Condo [](https://www.expedia.com/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America®ionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=CONDO) ## Check prices for these dates Tonight [Mar 25 - Mar 26](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-25&endDate=2026-03-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 26 - Mar 27](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-26&endDate=2026-03-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6005427&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windsor 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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.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) ### Berkshires Untold [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (880 reviews) "Beautiful little quaint hotel. I will definitely be returning" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin $78 nightly $87 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/7d4b7b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blooming Inn [](https://www.expedia.com/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) Shelburne Falls 9.2/10 Wonderful (133 reviews) "The bedroom and entire first floor living area was clean and nicely appointed in period decor. The self-check in process was simple and convenient. Lastly, the staff went above and beyond to find and quickly mail back my forgotten prescription eyeglasses to my home address. Will definitely stay here again if visiting the pioneer valley. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $143 nightly $154 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.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) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.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) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.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 (24 reviews) "Friendly staff, beautiful interiors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Izabela $139 nightly $155 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/6eebd994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/b8545843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn PLUS+ South Deerfield – Amherst [](https://www.expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) South Deerfield 7.2/10 Good (1,003 reviews) "Really nice place staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Omayra $85 nightly $95 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.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) ![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) ### Quality Inn Lee - Lenox South [](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) Lee 8.4/10 Very Good (1,000 reviews) "Cleanliness, staff courtesy, breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris $84 nightly $94 total Apr 8 - Apr 9 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![55-inch LCD TV with digital channels, printers](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/0a4a8480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/219287f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 King Bed (Room 4) | Desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/674accb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/20208a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revival House [](https://www.expedia.com/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information) Adams 9.0/10 Wonderful (26 reviews) "Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) melissa $150 nightly $168 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Adams-Hotels-The-Revival-House.h113486763.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.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) ### 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 (1,002 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 Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking | Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel [](https://www.expedia.com/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) Williamstown 9.2/10 Wonderful (896 reviews) "We love Cozy Corner. It's a snug, safe, well-maintained, home away from home. Love the ample breakfast and the genuine welcome we receive every time." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann $84 nightly $93 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/1fb7c9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room | Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/822e46eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/d1998883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villager Motel [](https://www.expedia.com/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) Williamstown 8.8/10 Excellent (783 reviews) "Very nice motel - well maintained and pleasant management" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cherie $75 nightly $84 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Standard Room, 1 King Bed, Non Smoking | Minibar, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/571ba9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/cf1063e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/ba6e7d9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/a9f8bbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn [](https://www.expedia.com/Adams-Hotels-Rodeway-Inn.h32052899.Hotel-Information) Adams 7.4/10 Good (240 reviews) "The frozen heater was extremely loud. Old and tired. Would not recommend however it was very inexpensive so you get what you pay for." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary $72 nightly $80 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Adams-Hotels-Rodeway-Inn.h32052899.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) ![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) ![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) ![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) ### 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 $101 nightly $111 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.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) ![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/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) ### 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 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/f3854c71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.com/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) Williamstown 9.6/10 Exceptional (599 reviews) "Very clean room. Service excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $99 nightly $111 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.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) ![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) ![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) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.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 (1,005 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 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Yankee-Inn.h54944.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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.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) ![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 (885 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick $121 nightly $135 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 (1,000 reviews) "Room was spotless, staff was very kind!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ilia $95 nightly $106 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/9722ad97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/45b65286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/8c32bd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area | Smart TV](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel [](https://www.expedia.com/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) New Ashford 9.4/10 Exceptional (94 reviews) "Great quaint place. Great staff and very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janelle $109 nightly $119 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/New-Ashford-Hotels-The-Springs-Motel.h95124564.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/870ad54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (295 reviews) "Friendly staff, great location, beautiful views, cozy room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth $151 nightly $169 total Mar 27 - Mar 28 Total with taxes and fees [](https://www.expedia.com/Lee-Hotels-Lakehouse-Inn.h15783244.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.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/1000000/30000/27900/27880/35c64b84.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 (839 reviews) "Clean room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Orlando $79 nightly $88 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/51c14a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/1f375131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/823465a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel [](https://www.expedia.com/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) Williamstown 9.4/10 Exceptional (315 reviews) "Great location with easy parking" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) David $77 nightly $87 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Williamstown-Hotels-Williamstown-Motel.h2758858.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=2026-04-08&endDate=2026-04-09®ionId=6005427&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%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Hotels.d6005427.Travel-Guide-Hotels) ## Top Windsor Hotel Reviews ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 8/10 Good "Staff was very accommodating. Room was ok but toilet didn’t flush without the water constantly running. Shower gel, shampoo & condition bottles were all empty in the shower. Had to call for new ones. " [](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg) ### Red Roof Inn PLUS+ South Deerfield – Amherst 8/10 Good "It’s ok." [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "very clean and friendly staff" [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![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 "Great, neat, convoy my son. " [](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great place to enjoy with the whole family!!!" [](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072_y.jpg) ### The Porches Inn at Mass MoCA 8/10 Good "It was a great stay at a place that was a cut above the usual hotel stay. Breakfast was provided but we only ate there 1 day for we wanted to experience things away from the place. There are many delicious places to eat for breakfast so try it. The location was perfect allowing for walking around whether to MOCA or finding other shops. While we didn’t bring our dog along this time, perhaps we will next time. " [](https://expedia.com/North-Adams-Hotels-The-Porches-Inn.h7662392.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 "Staff was pleasant! Clean and the restaurant was excellent!" [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/d239029a_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The exercise room is small. Not crowded. The pool was in use most of the time we were there as the pool is used for children's swimming lessons. We didn't want to use the hot tub with a bunch of kids and parents splashing around. Good staff and very responsive. " [](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Completely comfortable. Excellent restaurant. " [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## More cheap stays in Windsor ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA $79 nightly $88 total Mar 26 - Mar 27 Total with taxes and fees 7.6/10 Good! (839 reviews) [](https://expedia.com/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Quality Inn Lee - Lenox South](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn Lee - Lenox South 170 Housatonic Street Lee MA $84 nightly $94 total Apr 8 - Apr 9 Total with taxes and fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.com/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ South Deerfield – Amherst 9 Greenfield Rd South Deerfield MA $85 nightly $95 total Apr 12 - Apr 13 Total with taxes and fees 7.2/10 Good! (1,003 reviews) [](https://expedia.com/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.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 26 - Mar 27 Total with taxes and fees 9.2/10 Wonderful! (1,005 reviews) [](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/d8fde5b0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Berkshires-Lenox 445 Pittsfield Rd Lenox MA $103 nightly $115 total Apr 5 - Apr 6 Total with taxes and fees 9.2/10 Wonderful! (1,000 reviews) [](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Berkshire Hills Inn & Suites 1350 W Housatonic St Pittsfield MA $107 nightly $119 total Mar 29 - Mar 30 Total with taxes and fees 8.6/10 Excellent! (1,002 reviews) [](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Hotels in Windsor 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-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 92 properties [](https://expedia.com/3Star-Windsor-Hotels.s30-0-d6005427.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 49 properties [](https://expedia.com/2Star-Windsor-Hotels.s20-0-d6005427.Travel-Guide-Filter-Hotels) ## Find out more about Windsor ### Top reasons to visit Windsor - **Outdoor Adventures:** Windsor is a paradise for outdoor enthusiasts, offering skiing, hiking, and breathtaking scenery in nature reserves and mountains. - **Windsor Wine Country:** Savor delightful wine tastings in the picturesque Windsor Wine Country, perfect for a relaxing day. - **Charming Accommodations:** Enjoy a variety of lodging options, from cozy bed & breakfasts to relaxing resorts, catering to all travelers. - **Family-Friendly Activities:** Windsor offers family-friendly attractions and picnic spots, making it ideal for vacations with loved ones. - **Vibrant Local Culture:** Explore nearby downtown Healdsburg for a romantic atmosphere and diverse dining experiences. ### Find great hotels near Windsor Explore a range of delightful hotel accommodations in Windsor, Massachusetts, perfect for families, couples, and adventure seekers alike. Whether you're looking for a cozy bed & breakfast or a relaxing resort, Windsor offers various lodging options to suit your needs. Enjoy a memorable vacation experience with well-appointed suites and convenient access to local attractions. Start planning your getaway in this charming town today. - **[Berkshire Mountain Lodge: ](https://www.expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)** Berkshire Mountain Lodge is a charming 3-star lodge with a guest rating of 9.0, ideal for those seeking an adventurous vacation in the picturesque Berkshires. Located 13 miles from Windsor, this lodge is perfect for ski enthusiasts and golfers alike. With access to ski shuttles and lifts nearby, guests can enjoy exhilarating winter sports. For the summer adventurers, activities like kayaking, ziplining, and biking rentals are available nearby. The lodge also features on-site golf experiences, making it a versatile choice for those looking to immerse themselves in outdoor recreation year-round. - **[Holiday Inn & Suites Pittsfield-Berkshires by IHG: ](https://www.expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)** Holiday Inn & Suites Pittsfield-Berkshires by IHG is a welcoming 3-star hotel rated at 8.0, situated 11 miles from Windsor. This family-friendly hotel caters to adventurous spirits, offering a range of activities such as cross-country skiing, fishing, and horse riding in the nearby area. With amenities tailored for children, including free cribs and breakfast options, it ensures a comfortable stay for families. The property is conveniently located near a winery vineyard, making it an excellent choice for those looking to explore local flavors while enjoying a blend of relaxation and adventure. - **[Club Wyndham Bentley Brook: ](https://www.expedia.com/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information)** Club Wyndham Bentley Brook is a highly-rated 3-star hotel with a guest rating of 9.2, located 13 miles from Windsor. This property is a haven for ski lovers and adventure seekers, providing easy access to ski shuttles and lifts. Guests can enjoy on-site snowboarding and nearby cross-country skiing, as well as hiking opportunities. The inviting accommodations and excellent amenities make it a perfect retreat for those looking to indulge in winter sports while experiencing the breathtaking beauty of the Berkshires. ### Where to stay near Windsor Windsor, Massachusetts offers a perfect blend of outdoor adventure and scenic beauty, ideal for family-friendly vacations. Explore the charming local attractions, including the picturesque Windsor Wine Country, where you can indulge in delightful tastings. Nearby, the vibrant atmosphere of downtown Healdsburg invites you to enjoy its romantic ambiance and diverse dining options. Whether you're seeking an adventurous outing or a relaxing retreat, Windsor and its surroundings promise unforgettable experiences. - **[Pittsfield: ](https://www.expedia.com/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)** Located 11 miles from Windsor, Pittsfield is a vibrant city that offers an exciting mix of outdoor adventures and urban charm. Known for its skiing opportunities, visitors flock here during the peak months of June to August for thrilling sports experiences. With nearby ski resorts and fields, winter sports enthusiasts will find plenty to enjoy. The city's landscape is adorned with beautiful lakes and mountains, making it a picturesque destination year-round. Don't miss the local waterpark for family-friendly fun during the warmer months. - **[Hancock: ](https://www.expedia.com/Hancock-Hotels.d112303.Travel-Guide-Hotels)** Just 12 miles from Windsor, Hancock is another great destination for outdoor lovers. The city sees increased visitor numbers from March to April and again in July, thanks to its excellent skiing facilities. Hancock is surrounded by stunning mountains and serene lakes, perfect for both adrenaline-seeking adventurers and those looking to unwind in nature. The urban parks here provide ample space for relaxation and picnics, making it a well-rounded spot for visitors seeking both adventure and tranquility. - **[North Adams: ](https://www.expedia.com/North-Adams-Hotels.d9137.Travel-Guide-Hotels)** Situated 14 miles away from Windsor, North Adams blends culture and outdoor activities seamlessly. With peak travel seasons in June to July and September, this city attracts those interested in adventurous pursuits and cultural experiences. Visitors can enjoy live music concerts and explore the local art museum and cultural center, adding a unique flair to their experience. The public art scattered throughout the city enhances its artistic vibe, making it a wonderful place to wander and soak in the creative atmosphere. ### Things to do in Windsor Windsor, Massachusetts, is perfect for outdoor enthusiasts seeking adventure and stunning scenery. Visitors can enjoy skiing at nearby resorts and explore various ski fields. For a more relaxed experience, there are beautiful picnic spots where you can soak in the natural beauty of the area. Whether you're hitting the slopes or enjoying a leisurely day outdoors, Windsor offers a delightful escape for nature lovers and adventure seekers alike. **Shopping** In Windsor, you’ll find quaint shops offering unique gifts and local souvenirs. If you're up for a drive, head to the Lee Premium Outlets for brand-name bargains or explore the shops in nearby Great Barrington for a charming shopping experience. **Recreation** Experience tranquility at Kripalu Center for Yoga & Health, offering yoga classes and wellness workshops surrounded by nature. Explore the scenic hiking trails of the Berkshires for refreshing outdoor activities, or unwind with a soothing massage at a local spa to rejuvenate your mind and body. **Adventure** Explore Windsor State Forest for hiking and mountain biking amid picturesque landscapes and diverse wildlife. Try fishing or kayaking at nearby lakes for a refreshing outdoor experience. Don't miss the scenic views from the top of Mount Greylock, the highest peak in Massachusetts, offering thrilling adventures and stunning vistas. **Nightlife** In Windsor, Massachusetts, the nightlife is cozy and relaxed, featuring local pubs like The Windsor Tavern, where you can enjoy craft beers and live music. Nearby, outdoor events and seasonal festivals add to the vibrant atmosphere, making for a welcoming evening experience. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Windsor - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Windsor 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 Windsor is Tuesday. The most expensive day to stay in Windsor is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to customize your preferences, such as your budget, desired location, and type of hotel you’re looking for. To find the best prices and deals, simply arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by booking an Expedia package that combines your Windsor hotel stay with your flights and activities. ### Find the best attractions near Windsor Windsor, Massachusetts, is a haven for outdoor enthusiasts, offering stunning scenery and adventure opportunities. Explore its nature reserves and mountains, perfect for hiking and enjoying the great outdoors. Whether you're seeking thrilling adventures or a taste of local culture, Windsor's attractions promise memorable experiences for every traveler. Embrace the beauty and excitement of this charming destination. - **[Massachusetts Museum of Contemporary Art: ](https://www.expedia.com/Massachusetts-Museum-Of-Contemporary-Art-Hotels.0-l6091827-0.Travel-Guide-Filter-Hotels)** Experience the vibrant world of modern art at this expansive cultural center, showcasing innovative exhibitions and installations. The museum's unique architecture and engaging programming make it a must-visit for art enthusiasts. - **[Mount Greylock: ](https://www.expedia.com/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels)** Embrace adventure at Massachusetts' highest peak, where breathtaking scenery awaits. Enjoy hiking trails, stunning views, and the thrill of outdoor activities, making it a perfect spot for nature lovers and thrill-seekers alike. - **[Berkshire Museum: ](https://www.expedia.com/Berkshire-Museum-Hotels.0-l553248621532665288-0.Travel-Guide-Filter-Hotels)** Discover a blend of art, history, and science at this family-friendly museum. With interactive exhibits and engaging programs, the Berkshire Museum offers a fun and educational experience for visitors of all ages. ### Best time to go to Windsor The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, 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 | 19.9°F (-6.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 22.1°F (-5.5°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | | March | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 41.4°F (5.2°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | May | 53.8°F (12.1°C) | Light Rain | Mostly Sunny | Average | Average | | June | 61.5°F (16.4°C) | Light Rain | Mostly Sunny | Average | Average | | July | 67.6°F (19.8°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | August | 65.7°F (18.7°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly High | | September | 58.6°F (14.8°C) | Light Rain | Mostly Sunny | Average | Average | | October | 47.7°F (8.7°C) | Light Rain | Mostly Cloudy | Moderately High | Slightly High | | November | 35.4°F (1.9°C) | Light Rain | Mostly Sunny | Moderately High | Average | | December | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | ### The nearest major airports for your trip to Windsor When visiting Windsor, 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 44 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, and the [Marriott Hartford Downtown](https://www.expedia.com/Hartford-Hotels-Marriott-Hartford-Downtown.h1260819.Hotel-Information), 12 miles away. [ALB](https://www.expedia.com/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)any, NY (ALB-Albany Intl.), located 42 miles from Windsor, offers accommodations such as [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. For those considering Manchester, NH ([MHT](https://www.expedia.com/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)\-Manchester-Boston Regional), it's 87 miles away, featuring hotels like [The Grand at Bedford Village Inn](https://www.expedia.com/Manchester-Hotels-The-Bedford-Village-Inn.h1211321.Hotel-Information) and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.com/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information), both just 4 miles from the airport. ## Frequently asked questions ### What is the best area to stay in Windsor? > Windsor itself is a small, quiet town known for its natural beauty and outdoor activities. Staying near the town center provides easy access to the Windsor Historical Society and the local general store. This area is ideal for travelers seeking a peaceful retreat and proximity to hiking trails and scenic drives. > > > For couples looking for a tranquil getaway with access to nature, staying in a guesthouse or inn located in the hills surrounding the town center is an excellent choice. These accommodations often offer picturesque views and a chance to relax away from any hustle, while still being a short drive from attractions like the Windsor State Forest. ### When is the best time to go to Windsor? > Summer in Windsor offers pleasant temperatures, typically ranging from the mid-60s to high 70s Fahrenheit, making it ideal for exploring the natural beauty of the Berkshires. This season is great for hiking trails, enjoying the numerous lakes and ponds, and participating in local outdoor events. The longer daylight hours also allow for more extensive sightseeing. > > > For those who appreciate natural beauty, early to mid-fall is a spectacular time to visit. The Berkshire region is renowned for its vibrant autumn colors, with the hillsides transforming into a canvas of reds, oranges, and yellows. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Windsor 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 Windsor hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels) - [Savoy Hotels ](https://www.expedia.com/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Cabin Rentals in Savoy ](https://www.expedia.com/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [B&B in Savoy ](https://www.expedia.com/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in Savoy ](https://www.expedia.com/Savoy-Cottages.d6005417-aaCottages.Travel-Guide-Accommodation) - [Peru Hotels ](https://www.expedia.com/Peru-Hotels.d553248634999167831.Travel-Guide-Hotels) - [Hotels near Bas Ridge Golf Course ](https://www.expedia.com/Bas-Ridge-Golf-Course-Hotels.0-l553248621560926698-0.Travel-Guide-Filter-Hotels) - 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