Title: Book The Best Hotels in Cheshire, MA for 2026 from CA $97 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 Cheshire Pool [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&amenities=POOL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&travelerType=family_friendly) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&amenities=PETS) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&amenities=HOT_TUB) Farm [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&lodging=AGRITOURISM) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&lodging=COTTAGE) Condo [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&lodging=CONDO) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-04-05&d1=2026-04-05&endDate=2026-04-07&d2=2026-04-07&lodging=CABIN) ## Check prices for these dates Tonight [Mar 22 - Mar 23](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-22&endDate=2026-03-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 23 - Mar 24](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-23&endDate=2026-03-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire hotels ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53 reviews) "Nice place for a weekend away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $324 CA $343 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/c0f1d776.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) ![Standard Room, 1 Queen Bed, Non Smoking](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.ca/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 CA $109 CA $128 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.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) ![Standard Room, 1 King Bed, Non Smoking](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](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.ca/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 CA $115 CA $129 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.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](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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villager Motel [](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) Williamstown 8.8/10 Excellent (781 reviews) "Very nice motel - well maintained and pleasant management" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cherie CA $103 CA $115 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/7b825179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Shared Dormitory](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/f69b88ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/542dbb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UU Rowe Camp and Conference Center [](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information) Rowe 10/10 Exceptional (1 review) "Yes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stuart CA $309 CA $326 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.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) ![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/25f05b7c.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) ![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maple Terrace Motel [](https://www.expedia.ca/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 CA $136 CA $152 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.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) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.ca/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 CA $146 CA $163 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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) ![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) ![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,002 reviews) "Easy check-in; accommodating staff; clean room. Convenient but also quiet location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaniel CA $121 CA $135 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.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) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.8/10 Exceptional (23 reviews) "Friendly staff, beautiful interiors." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Izabela CA $191 CA $213 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.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 (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) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.ca/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 CA $145 CA $160 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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.ca/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 CA $108 CA $121 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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)](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) ![Reception](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/f9501b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revival House [](https://www.expedia.ca/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 CA $206 CA $230 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.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) ![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/c8b24996.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.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) Shelburne Falls 9.2/10 Wonderful (133 reviews) "Beautiful comfortable home with many thoughtful touches" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $128 CA $211 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/f94cd23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/86a5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/954b171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/d0c9280e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Vista Motor Lodge [](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information) North Adams 9.8/10 Exceptional (207 reviews) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALEKSey CA $249 CA $264 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/adb513b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/be737544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/19354f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/4e6dafd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Williamstown [](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) Williamstown 8.8/10 Excellent (407 reviews) "Stayed one night...great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberley CA $217 CA $242 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/320c2d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Studio Sofabed Non Smoking | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/w3837h2559x0y0-777976aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) Lenox 9.2/10 Wonderful (1,001 reviews) "Great stay, great breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $142 CA $158 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/571ba9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/ee5af5b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/46ef42a3.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.ca/Adams-Hotels-Rodeway-Inn.h32052899.Hotel-Information) Adams 7.4/10 Good (240 reviews) "The room was clean and nice but i was confusing about the abandoned vehicles directly behind the hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $99 CA $110 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Adams-Hotels-Rodeway-Inn.h32052899.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/65150c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/1134ca16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/dccac924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/2649134b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willows Motel Williamstown [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) Williamstown 9.0/10 Wonderful (1,000 reviews) "Older building and decor but rooms are in impeccable condition and amazingly clean for their age. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete CA $111 CA $124 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.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) ![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) ![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) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (87 reviews) "Amazing stuff they went above and beyond to accommodate on fridge cold day, good breakfast, hot tub is amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paulo Eduardo CA $181 CA $202 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.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](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/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 CA $182 CA $214 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.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.ca/Hotel-Search?startDate=2026-04-05&endDate=2026-04-06®ionId=6005398&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Hotels.d6005398.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Hotels.d6005398.Travel-Guide-Hotels) ## Stay near popular Cheshire attractions ### St Mary's of the Assumption Church St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views, or seek out its ski slopes. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665539) ## Learn more about Cheshire Get away to romantic Cheshire! Enjoy the skiing, hiking, and lake views. [See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2026-04-05&endDate=2026-04-06&adults=2®ionId=6005398) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=900&h=599&p=1&q=high) ## Top Cheshire Hotel Reviews ## Recent Reviews in Cheshire ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "This is our 3rd year staying here for my son’s birthday in March. Affordable and having the 2 rooms with a kitchen is so nice. My son’s favorite part is the pool which is always warm and clean, never smells too strong like some places. Hot tub feels amazing too. Will be back next year, or sooner :)" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 4/10 Poor "Hotel under construction/renovations. No hot water for morning shower." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "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." [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "one of my favorite places to stay..." [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg) ### The Cornell Inn, Lenox & The Berkshires 10/10 Excellent "Clean, quiet, and a great breakfast! The staff was friendly. We enjoyed a fire in our room and the free bottle of wine. " [](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.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 6/10 Okay "rooms have a weird smell, if the hotel is empty" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/ef3ce5c5_y.jpg) ### Hotel On North 10/10 Excellent "The hotel was even more beautiful in person! Rooms were incredibly spacious and lovely. The staff was incredibly friendly and helpful. Great stay would definitley return. " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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 "yes" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Easy check-in; accommodating staff; clean room. Convenient but also quiet location." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ## More cheap stays in Cheshire ![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 CA $108 CA $121 total Mar 23 - Mar 24 includes taxes & fees 7.6/10 Good! (839 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Berkshire Inn](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Berkshire Inn 150 W Housatonic St Pittsfield MA CA $109 CA $122 total Mar 23 - Mar 24 includes taxes & fees [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.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 CA $115 CA $129 total Apr 6 - Apr 7 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA CA $121 CA $135 total Mar 23 - Mar 24 includes taxes & fees 9.2/10 Wonderful! (1,002 reviews) [](https://expedia.ca/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 CA $142 CA $158 total Apr 5 - Apr 6 includes taxes & fees 9.2/10 Wonderful! (1,001 reviews) [](https://expedia.ca/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 CA $146 CA $163 total Mar 25 - Mar 26 includes taxes & fees 8.6/10 Excellent! (1,000 reviews) [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Hotels in Cheshire with star rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 11 properties [](https://expedia.ca/4Star-Cheshire-Hotels.s40-0-d6005398.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 108 properties [](https://expedia.ca/3Star-Cheshire-Hotels.s30-0-d6005398.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 102 properties [](https://expedia.ca/2Star-Cheshire-Hotels.s20-0-d6005398.Travel-Guide-Filter-Hotels) ## Find out more about Cheshire ### Top reasons to visit Cheshire - **Outdoor Adventures:** Cheshire is a haven for outdoor enthusiasts, featuring excellent skiing and scenic hiking opportunities. - **Charming Local Culture:** Explore the quaint Cheshire Village and visit the Cheshire Military Museum for a taste of local history. - **Vibrant Nightlife:** Unwind at various pubs and local theatres after a day of adventure. - **Beautiful Scenery:** Enjoy the picturesque landscapes and scenic mountains that surround the area. - **Diverse Accommodations:** Find a range of hotels and resorts catering to families, couples, and adventurers alike. ### Find great hotels near Cheshire Discover the charm of Cheshire, Massachusetts, where a variety of hotels and resorts await to enhance your stay. Whether you’re seeking a family-friendly retreat, a romantic getaway, or an adventure-filled vacation, Cheshire offers accommodations that cater to all your needs. Explore the best Cheshire hotels for a memorable experience, and find the perfect spot to unwind while enjoying the scenic beauty of this delightful town. - **[Holiday Inn & Suites Pittsfield-Berkshires by IHG: ](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)** Nestled in the heart of Pittsfield, only 14.5km from Cheshire, this 3-star hotel is perfect for families and adventure seekers alike. The property boasts a range of outdoor activities such as snowboarding, hiking, horseback riding, and fishing, making it an excellent choice for those looking to embrace the great outdoors. Families will appreciate the child-friendly amenities, including free cribs and window guards for safety. With its city-themed atmosphere and recreational options nearby, this hotel promises a memorable stay filled with excitement and exploration. - **[Club Wyndham Bentley Brook: ](https://www.expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information)** Situated just 9.7km from Cheshire, Club Wyndham Bentley Brook is a 3-star resort tailored for ski enthusiasts and adventure lovers. With convenient access to ski shuttles and lifts, guests can hit the slopes in no time. The property features onsite snowboarding and is near hiking and downhill skiing locations, making it an ideal retreat for winter sports enthusiasts. Enjoy the inviting atmosphere and easy access to thrilling outdoor activities that will satisfy your adventurous spirit. - **Hotel Downstreet, Ascend Hotel Collection:** Located 16.1km from Cheshire, Hotel Downstreet is a welcoming 3-star hotel that embraces inclusivity and pet-friendly policies. Ideal for LGBTQIA travellers, the property is affiliated with LGBTQI travel guides and allows pets, ensuring everyone feels at home. With amenities catering to dogs and cats, guests can enjoy their stay without leaving their furry friends behind. This hotel blends comfort and community, making it a great choice for those seeking a warm and welcoming atmosphere. ### Where to stay near Cheshire Cheshire, Massachusetts, offers a delightful blend of adventure and family-friendly experiences, making it an ideal vacation spot. From picturesque locations perfect for weekend getaways to romantic escapes, visitors can explore charming neighborhoods nearby. Enjoy skiing and outdoor activities while soaking in the scenic beauty. With convenient access to lovely locations, Cheshire provides a memorable atmosphere for every type of traveller, whether you're seeking adventure or a peaceful retreat. - **[Williamstown: ](https://www.expedia.ca/Williamstown-Hotels.d7859.Travel-Guide-Hotels)** Nestled 17.7km from Cheshire, Williamstown is a charming city renowned for its vibrant arts scene, historic college university, and stunning natural landscapes. Visitors flock here year-round, with peak seasons in April and June to July, drawn by the allure of skiing and adventure sports. The nearby ski fields and resorts offer excellent winter activities, while the picturesque mountains and tranquil lake provide a perfect backdrop for outdoor exploration. Whether you're hitting the slopes or strolling through the town's cultural landmarks, Williamstown promises a delightful travel experience. - **[Pittsfield: ](https://www.expedia.ca/Pittsfield-Hotels.d9478.Travel-Guide-Hotels)** Located just 14.5km from Cheshire, Pittsfield is a dynamic city that comes alive during peak summer months from June to August. Known for its adventurous spirit, this city offers ample opportunities for skiing, as well as access to a stunning lake and mountain scenery. The local waterpark adds an extra element of fun for families, making it a versatile destination for travellers. With its rich history and community events, Pittsfield provides a warm and welcoming atmosphere, perfect for anyone looking to immerse themselves in local culture while enjoying the great outdoors. - **[North Adams: ](https://www.expedia.ca/North-Adams-Hotels.d9137.Travel-Guide-Hotels)** Just 16.1km away from Cheshire, North Adams is a vibrant city that embraces adventure and creativity. Known for its thriving arts community, this city features a renowned art museum and numerous public art installations that invite exploration. With peak visitor numbers in June to July and September, North Adams attracts those seeking outdoor fun and skiing experiences. The surrounding mountains provide fantastic hiking opportunities, while the cultural centre fosters a lively environment for arts and entertainment. North Adams offers a unique blend of nature and culture, ensuring an unforgettable vacation experience. ### Things to do near Cheshire Cheshire, Massachusetts, is perfect for outdoor enthusiasts and adventure seekers, offering fantastic skiing opportunities at its local ski resorts and fields. Visitors can enjoy scenic walks, vibrant nightlife, and a variety of pubs to unwind after a day on the slopes. For those looking to relax, the area also features charming local theatres and championship golf courses, making it an ideal destination for a well-rounded vacation experience. **Shopping** Cheshire offers a quaint shopping experience with local charm. For a broader selection, head to the North Adams Center, North Adams Gateway Center, or Colonial Plaza, all located 16.1km away, featuring a mix of business and family vibes. If you're up for a drive, you'll find more unique shops along the way. **Recreation** [Skyline Country Club](https://www.expedia.ca/Skyline-Country-Club-Hotels.0-l553248621532665295-0.Travel-Guide-Filter-Hotels) offers a scenic golf experience with stunning views and outdoor sports activities, perfect for golf enthusiasts. For a more tranquil atmosphere, visit [Windsor Lake Park](https://www.expedia.ca/Windsor-Lake-Park-Hotels.0-l553248621560926712-0.Travel-Guide-Filter-Hotels), where you can unwind amidst nature and enjoy wellness-focused relaxation. [Waubeeka Golf Links](https://www.expedia.ca/Waubeeka-Golf-Links-Hotels.0-l553248621561173643-0.Travel-Guide-Filter-Hotels) also provides an excellent golfing experience surrounded by beautiful landscapes. **Adventure** At [Jiminy Peak Mountain Resort](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels), experience thrilling skiing and winter sports vibes only 11.3km from Cheshire. At [Berkshire East Ski Resort](https://www.expedia.ca/Berkshire-East-Ski-Resort-Hotels.0-l553248621532666707-0.Travel-Guide-Filter-Hotels), 24.1km away, enjoy outdoor adventures amidst breathtaking scenery. For hiking enthusiasts, the [Skyline Trail](https://www.expedia.ca/Skyline-Trail-Hotels.0-l553248621532666608-0.Travel-Guide-Filter-Hotels), also 24.1km from Cheshire, offers stunning views and a true adventure experience. **Nightlife** Experience the vibrant nightlife in Cheshire by attending a show at the [Williamstown Theatre Festival](https://www.expedia.ca/Williamstown-Theatre-Festival-Hotels.0-l553248621532665542-0.Travel-Guide-Filter-Hotels) or the [Adams Theater](https://www.expedia.ca/Adams-Theater-Hotels.0-l811533410309558272-0.Travel-Guide-Filter-Hotels), both offering a mix of culture and entertainment. For something more adventurous, take a thrilling ride at the Alpine Super Slide, adding excitement to your evening. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Cheshire To save money during your visit to Cheshire, plan your trip for the cheaper months of March to April or November, and aim for a Tuesday stay, as Saturdays tend to be pricier. Use Expedia’s search tool to find budget-friendly accommodations by sorting results from lowest to highest prices and applying filters for eco-friendly options. Consider booking a package that combines your hotel, flights, and activities for additional savings. Lastly, take advantage of free local attractions and consider using public transport to keep your costs down while exploring the area. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Cheshire are March to April and November, 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 Cheshire is Tuesday. The most expensive day to stay in Cheshire is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to set your budget, choose your desired location, and much more. You can easily arrange your search results from the lowest to highest prices, ensuring you find the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type. For instance, selecting the Eco-certified filter will display sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your hotel stay in Cheshire with your flights and activities through an Expedia package. ### Find the best attractions near Cheshire Cheshire, Massachusetts, is an excellent destination for outdoor enthusiasts, offering skiing, adventure, and various cultural experiences. Key points of interest include the local library, scenic mountains, and arts centre. Visitors can explore the Cheshire Military Museum, the charming Cheshire Village, and nearby attractions like Chester, the Cheshire Ring, and Cheshire Oaks, making it a delightful spot for families and culture seekers alike. - **[Mount Greylock: ](https://www.expedia.ca/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels)** Experience the beauty of Massachusetts' highest peak, just 8.0km from Cheshire. This mountain offers stunning vistas and thrilling outdoor adventures, perfect for hiking and nature photography. - **[Mount Greylock State Reservation Visitor Center: ](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels)** Located 4.8km away, this visitor centre is an ideal spot for families. It provides information on the area's natural wonders and access to various outdoor activities, ensuring a fun-filled day for all ages. - **[Williams College: ](https://www.expedia.ca/Williams-College-Hotels.0-l6091833-0.Travel-Guide-Filter-Hotels)** A historic institution situated 16.1km from Cheshire, Williams College boasts a rich cultural atmosphere. Explore its beautiful campus, art galleries, and vibrant community events that reflect the college's esteemed heritage. ### Best time to go to Cheshire The best time to visit Cheshire is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately 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 | 19.9°F (-6.7°C) | Light Rain | Mostly Cloudy | Average | Average | | 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 | Moderately High | 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 High | 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 | Average | Slightly High | | November | 35.4°F (1.9°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | December | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Moderately Low | Average | ### The nearest major airports for your trip to Cheshire When visiting Cheshire, Massachusetts, you can fly into several major airports. Bradley International Airport ([BDL](https://www.expedia.ca/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)) in Hartford, CT, is 80.5km away, with nearby accommodations like the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1.6km from the airport. Albany International Airport ([ALB](https://www.expedia.ca/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)) is closer at 56.3km and offers options such as the [Park Manor Hotel](https://www.expedia.ca/Clifton-Park-Hotels-Park-Manor-Hotel.h895584.Hotel-Information), located 12.9km away. The nearest airport is Pittsfield Municipal Airport (PSF), only 19.3km from Cheshire, where you can stay at [The Central Downtown Inn & Suites](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information), just 3.2km from the airport. Each airport provides convenient access to nearby hotels for your stay. ## Frequently asked questions ### What is the best area to stay in Cheshire? > This central area offers a classic New England village experience. Main Street is where you'll find the local post office, a few small shops, and the town hall, all within a short walk of each other. The layout is quite simple, with residential streets branching off the main thoroughfare, and it's generally easy to navigate. > > > Couples looking for a relaxing escape will find the village centre appealing. It's a great base for enjoying the natural beauty of the Berkshires, with easy access to scenic drives and walks. The proximity to local eateries means a convenient evening out without needing to travel far. > > > For those planning to explore the wider Berkshire region by car, staying near the main roads that pass through Cheshire, such as Route 8, offers excellent convenience. ### What are the best family hotels in Cheshire? > This 3.5-star inn boasts an impressive 9.6 rating and is highly recommended for families. It offers convenient connecting rooms, which are ideal for larger families, and many rooms provide stunning mountain views. Guests particularly appreciate the complimentary full breakfast and free WiFi. The inn is also well-located for exploring the outdoors, being just 7.6 km from Mount Greylock State Reservation. ### What hotels in Cheshire offer free breakfast? > The 3.5-star Harbour House Inn, with an outstanding 9.6 rating, provides guests with both free breakfast and a full breakfast option. This hotel is praised for its tranquil mountain views and its convenient amenities, including free toiletries, free self-parking, and free WiFi. It is also well-located for exploring the area, with Mount Greylock State Reservation just 7.6 kilometres away. Find more [hotels with free breakfast in Cheshire](https://www.expedia.ca/Cheshire-Hotels-Hotels-With-Free-Breakfast.0-0-d6005398-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) ### What are the most romantic hotels in Cheshire for couples? > This 3.5-star inn, with an impressive 9.6 rating, is celebrated for its beautiful mountain views, making it ideal for a romantic escape. Guests can enjoy a complimentary full breakfast, and the inn also provides free toiletries, free self-parking, and free WiFi. Its proximity to Mount Greylock State Reservation, just 7.6 km away, offers opportunities for scenic walks and enjoying nature together. See all [romantic hotels in Cheshire](https://www.expedia.ca/Cheshire-Hotels-Romantic-Hotel.0-0-d6005398-tRomanticHotel.Travel-Guide-Filter-Hotels) ### What are the best hotels in Cheshire near Mount Greylock State Reservation? > The 3.5-star Harbour House Inn, with an outstanding 9.6 rating, is located approximately 7.6 kilometres from Mount Greylock State Reservation, making it a convenient base for exploring the area. Guests frequently appreciate the complimentary full breakfast and free Wi-Fi. The hotel also offers connecting rooms, which is a great feature for families travelling together, and many rooms boast lovely mountain views. ### When is the best time to go to Cheshire? > During these months, the Berkshire Mountains offer ideal conditions for hiking, cycling, and exploring the natural beauty of the area. The foliage in autumn, particularly in late September and early October, is especially stunning, drawing many visitors to witness the vibrant colours. This period also sees the most local events and farmers' markets, adding to the experience. > > > For those interested in winter sports, the months of December through March offer opportunities for skiing and snowboarding at nearby resorts, though Cheshire itself is primarily a quiet, residential town without its own ski slopes. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Cheshire hotel booking with Expedia? ### How much is the nightly rate at a Cheshire hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Farmstay in Adams ](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams ](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams ](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams ](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - 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