Title: Book the Best Cheshire LUXURY Hotels - Upscale Hotels in Cheshire, MA | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[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) # Find luxury hotels in Cheshire, MA - ![](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 ## Check availability on Cheshire Luxury Hotels Tonight [Jan 4 - Jan 5](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-04&endDate=2026-01-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-05&endDate=2026-01-06&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-16&endDate=2026-01-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Cheshire Hotel Reviews ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak! " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "The stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too! " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "This is the second time I’ve stayed at The Black Swan for the holidays while visiting my family. I like the fact that breakfast is included and they have everything from the traditional “continental” breakfast fare to hard-boiled eggs and microwave-able breakfast sandwiches. I also like the in-room Keurig coffee maker. The guest WiFi was great - no buffering. " [](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/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Staff is incredibly helpful and friendly " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "A wonderful property with excellent amenities. The heated outdoor pool and sauna were clean and easily accessible. I travel with my small dog and my room was great. They actually upgraded me to a suite! I would stay here again without question. It is across the street from Mass MOCa, an extraordinary museum. Staff was courteous and helpful. " [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Courteous staff " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Loved having coffee and tea 24/7" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury holiday in Cheshire? ### When can I expect good weather in Cheshire? ### What's there to see and do in Cheshire? ## Explore a world of travel with Expedia - Lodging - Flights - 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