Title: Book The Best Hotels in Cheshire, MA for 2025 from CA $117 - 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) ![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find hotels in Cheshire, MA from CA $117 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&lodging=CABIN) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&travelerType=family_friendly) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&lodging=APARTMENT) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&amenities=HOT_TUB) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&lodging=COTTAGE) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&amenities=PETS) 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=2025-10-20&d1=2025-10-20&endDate=2025-10-22&d2=2025-10-22&lodging=CONDO) ## Check prices for these dates Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 1,007 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.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) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.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/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " CA $351 CA $372 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.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/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1003) "Great Indian restaurant in the hotel!" CA $148 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1002) "Nice area to visit " CA $187 CA $209 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (745) "Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. " CA $122 CA $136 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2039) "Really nice place at a reasonable price" CA $92 CA $118 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (892) "Excellent customer service and great rooms" CA $144 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1003) "We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect." CA $178 CA $254 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee 9.0/10 Wonderful (748) "The lodging was convenient to all the area attractions." CA $162 CA $200 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/433bbf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1000) "Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool" CA $193 CA $216 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (676) "Very convenient set up of both room and kitchen, resort very easy to navigate. " CA $130 CA $176 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/e9560cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huttopia Berkshires Williamstown 10/10 Exceptional (4) "Perfect place for a relaxing getaway! We loved everything! " CA $137 CA $153 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1006) "great place have stayed several times, and hope to return." CA $202 CA $289 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.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/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.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 Pittsfield 9.4/10 Exceptional (51) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" CA $200 CA $224 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn Williamstown 9.6/10 Exceptional (513) "Great hotel, staff and restaurant!" CA $278 CA $311 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (777) "Great property! Very large clean room in a unique hotel! " CA $172 CA $192 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/3e40d6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/f6ede23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/7720f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel Williamstown 9.4/10 Exceptional (303) "The rooms are dated but very clean and neat. This family run motel is convenient to everything in Williamstown and the university. The check-in was easy and staff were knowledgeable and kind." CA $104 CA $117 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn)](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/w2880h1917x0y0-550a94f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.4/10 Very good (549) "Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. " CA $128 CA $143 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/f5e7ded9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/962c72ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mountain view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/15afb24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/ddd4b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Williamstown Williamstown 6.6/10 (884) "Great affordable place to stay while in the northern Berkshires." CA $153 CA $171 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information) ![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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1000) "Great property would certainly stay again." CA $142 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/ae684309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Extended Stay)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/c71b3d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room (Superior King Bed with a Porch)](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/aaec0515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA North Adams 9.4/10 Exceptional (425) "Great hotel, lovely pool and hot tub. We got upgraded to a suite!" CA $248 CA $308 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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=2025-10-20&endDate=2025-10-21®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) ## Learn more about Cheshire Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting. [See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-10-20&endDate=2025-10-21&adults=2®ionId=6005398) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Ed Gaffny ### Stay near popular Cheshire attractions [](https://expedia.ca/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532665539) ## More cheap stays in Cheshire ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd, Routes 7 and 20, Lenox, MA CA $110 CA $123 total Oct 19 - Oct 20 includes taxes & fees 7.4/10 Good! (802 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![FairBridge Inn Express](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### FairBridge Inn Express 16 Cheshire Road, Pittsfield, MA CA $112 CA $125 total Oct 7 - Oct 8 includes taxes & fees 5.2/10 (785 reviews) [](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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 $187 CA $209 total Nov 2 - Nov 3 includes taxes & fees 9/10 Wonderful! (1,014 reviews) [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Berkshire Hills Inn & Suites 1350 W Housatonic St, Pittsfield, MA CA $142 CA $158 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 1055 South Street, Pittsfield, MA CA $200 CA $224 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (45 reviews) [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street, Lee, MA CA $129 CA $144 total Oct 26 - Oct 27 includes taxes & fees 8.2/10 Very Good! (1,008 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ## Hotels in Cheshire with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_w.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/12000000/11450000/11449200/11449113/a007f019_w.jpg) 3 Star Hotels 99 properties [](https://expedia.ca/3Star-Cheshire-Hotels.s30-0-d6005398.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_w.jpg) 2 Star Hotels 89 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. ## Recent reviews of Cheshire hotels ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 5/5 Excellent "Clean place. Good breakfast and friendly staff" A verified traveller from Carmichael stayed at Best Western Plus Berkshire Hills Inn & Suites Posted 4 days ago [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 5/5 Excellent "Great place! Food excellent ss well!" A verified traveller stayed at The Red Lion Inn Posted 6 days ago [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 5/5 Excellent "I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast." A verified traveller stayed at The Yankee, Trademark Collection by Wyndham Posted 6 days ago [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 5/5 Excellent "Great!" A verified traveller stayed at Vacation Village in the Berkshires Posted 6 days ago [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 5/5 Excellent "There was construction noise next door." A verified traveller stayed at Hotel On North Posted 7 days ago [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 5/5 Excellent "The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane." A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel Posted 7 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 5/5 Excellent "Lovely place with lovely people. Food is great. " A verified traveller stayed at The Williams Inn Posted 7 days ago [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 5/5 Excellent "Absolutely loved this place. It was quant, hip, affordable and just all around stunning! Worth it all! Would stay there again in a heartbeat. " A verified traveller from Rochester stayed at Berkshires Untold Posted 7 days ago [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 5/5 Excellent "A bit out dated but nice area for fireplace during winter overlooking the pool. Rugs need to go in the hallways, they are UGLY! Service was friendly, the rooms are equiped with utensils, fridge, microwave etc and spacious. Hot tub and grills. Recommend" A verified traveller stayed at Berkshire Mountain Lodge Posted 7 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Cheshire? > The most popular time to visit Cheshire is during the summer months, particularly July and August. At this time, the climate is pleasantly warm, with average temperatures ranging from 17 to 22°C, making it superb for exploring the stunning countryside and charming towns. > > > > During the peak season of June to August, Cheshire comes alive with a variety of outdoor activities and events. Attractions such as the beautiful Tatton Park and the historic Chester Zoo are bustling with families and nature enthusiasts alike. The delightful weather lends itself to leisurely walks along the picturesque canals or through the scenic gardens, allowing you to fully immerse yourself in the region's natural beauty. > > > > For couples seeking romance, these summer months offer vibrant festivals, open-air concerts, and various local events that showcase Cheshire's rich heritage. Imagine indulging in al fresco dining at one of the many quaint bistros, where you can enjoy seasonal dishes made from local produce while soaking up the lively atmosphere. > > > > If you're looking for a slightly quieter experience, consider visiting in September. This month often sees fewer crowds while still enjoying lovely weather and the beautiful autumn colours beginning to emerge. You'll be able to explore the area at a more leisurely pace and perhaps take advantage of some off-peak pricing on accommodations and activities. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Cheshire hotel for you. ### How can I save on a Cheshire hotel booking with Expedia? > Before booking your Cheshire hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Cheshire hotel? > Prices for hotels in Cheshire often vary, but you can find a great deal from CA $117 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)