Title: 4 Stars Hotels in Cheshire, Massachusetts from CA $146 - Find Cheap Cheshire Hotels With 4 Stars | Expedia.ca [Cheshire Travel Guide](https://expedia.ca/Cheshire.dx6005398)[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)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[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 ## Check availability on Cheshire 4 Star Hotels Tonight [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-14&endDate=2026-01-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-15&endDate=2026-01-16&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire 4-star hotels ![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) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/30e56504.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) ### The Williams Inn [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) Williamstown 9.6/10 Exceptional (561 reviews) "Very pleasant and relaxing place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steve CA $258 CA $289 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/8d37b75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (354 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $130 CA $146 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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) ![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) ![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) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.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 (290 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $184 CA $216 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/6fb5c35e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (134 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/9d4b10ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/3c58b600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/ee47037f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/16000000/15700000/15691300/15691251/ceae03ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seven Hills Inn [](https://www.expedia.ca/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) Lenox 7.8/10 Good (467 reviews) "Great location, nice breakfast and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lenox-Hotels-Seven-Hills-Inn.h15691251.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $530 CA $641 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74 reviews) "Beautiful place. Wonderful owner and staff. Our stay there was a total delight." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $542 CA $606 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/2ae49251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/fbe29a4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/84d1c1bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/34000000/33510000/33509100/33509020/32a90503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### General Williams Estate House Lenox/Stockbridge [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) Stockbridge 9.8/10 Exceptional (113 reviews) "The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanna T. [](https://www.expedia.ca/General-Williams-Estate-House-LenoxStockbridge.h33509020.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Terrace Inn [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) Lenox 9.0/10 Wonderful (43 reviews) "Beautiful historic house in a great location. Responsive owner. Great visit!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abby CA $304 CA $339 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/b5bad44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/c5b973e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) Lee 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/0eb6e44a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/f210c5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/7ddf77a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/900000/893700/893627/ac720fcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garden Gables Inn [](https://www.expedia.ca/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) Lenox 9.2/10 Wonderful (57 reviews) "Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john [](https://www.expedia.ca/Lenox-Hotels-Garden-Gables-Inn.h893627.Hotel-Information) ![](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%2F4Star-Cheshire-Hotels.s40-0-d6005398.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Cheshire-Hotels.s40-0-d6005398.Travel-Guide-Filter-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=2026-01-28&endDate=2026-01-29&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 ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Accommodating staff!" [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## Find out more about Cheshire If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Cheshire are calling your name. Known for providing first-rate service in amazing locations, each of the Cheshire 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Cheshire. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Cheshire, Massachusetts, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Cheshire hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Cheshire? > - Search for the lowest price from CA $146 ### What's the difference between 5-star and 4-star hotels in Cheshire? ### Does Cheshire have any 4-star all-inclusive resorts? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in East Village Historic District ](https://www.expedia.ca/2Star-East-Village-Historic-District-Amherst-Hotels.s20-n553248621557920008-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in South End ](https://www.expedia.ca/2Star-South-End-Springfield-Hotels.s20-n898868902485037056-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Franklin ](https://www.expedia.ca/3Star-Franklin-Hotels.s30-0-d601800.Travel-Guide-Filter-Hotels) - 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