Title: The Best Cheshire, MA Chalets from $793 | Expedia.com [Cheshire Travel Guide](https://expedia.com/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.com/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.com/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6005398&startDate=2026-07-31&endDate=2026-08-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire chalets ![Exterior](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/84aaf038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/062c285e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/w1200h799x0y1-17216d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/111000000/110260000/110251200/110251122/8836ff52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Luxurious Chalet with heated Pool,Hot Tub, Game Rooms. Pet-Friendly! [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) Cropseyville 10/10 Exceptional (3 reviews) "Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick H. $1,330 nightly $1,476 total May 6 - May 7 Total with taxes and fees [](https://www.expedia.com/Cropseyville-Hotels-Sleeps-16-Hot-Tub-Private-Heated-Pool-Fire-Pit-Game-Room.h110251122.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/225c30fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/c8edb36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/ba39107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, books](https://images.trvl-media.com/lodging/124000000/123360000/123354300/123354233/3201c410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) Charlemont 10/10 Exceptional (2 reviews) "Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Georgia P. $710 nightly $793 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Charlemont-Hotels-Joia-Verde-ChaletSleeps-8.h123354233.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-20&endDate=2026-04-21®ionId=6005398&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CABIN) Cottages [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=COTTAGE) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VACATION_HOME) Condos [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CONDO) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APART_HOTEL) Apartments [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=VILLA) Chalets [](https://www.expedia.com/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2026-07-05&d1=2026-07-05&endDate=2026-07-08&d2=2026-07-08&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Chalets.d6005398-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Chalets.d6005398-aaChalets.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![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 "Always a pleasant experience. We stay once a year" [](https://expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Very good " [](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 10/10 Excellent "Rooms have been updated (bathroom was great) and clean. Some updates may still be happening on the rooms on the 3rd floor," [](https://expedia.com/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Love that place. Does need a little sprucing up. Staff great and accomodating " [](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 8/10 Good "solid 4 stars, clean and comfy rooms" [](https://expedia.com/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/d239029a_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 6/10 Okay "Loud refrigerator overall 2.5 stars in terms of condition of the hotel Staff is friendly " [](https://expedia.com/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 10/10 Excellent "Very clean and updated. Park right outside your room. Nice bar with outdoor fireplace. Staff was amazing. Simple put, great place to stay!" [](https://expedia.com/Lenox-Hotels-Berkshires-Untold.h76297618.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 6/10 Okay "Great dinner, nice room. Only complaint is that none of the 3 elevators would come to the 6 floor in the morning. It was a long walk with our baggage." [](https://expedia.com/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375_y.jpg) ### Vacation Village in the Berkshires 8/10 Good "Beds could be more updated" [](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ## Find out more about Cheshire ## Cheshire Chalets information | Number of reviews | 5 | | ----------------- | --------- | | Accommodation | 6 Chalets | | Lowest Price | $793 | | Highest Price | $1,476 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near St Mary's of the Assumption Church ](https://www.expedia.com/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels) - [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [B&B in Lanesborough ](https://www.expedia.com/Lanesborough-Bed-And-Breakfast.d6005408-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Apartments in Lanesborough ](https://www.expedia.com/Lanesborough-Apartments.d6005408-aaApartments.Travel-Guide-Accommodation) - [Cottages in Lanesborough ](https://www.expedia.com/Lanesborough-Cottages.d6005408-aaCottages.Travel-Guide-Accommodation) - [Cabin Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Cabins.d6005408-aaCabins.Travel-Guide-Accommodation) - [Resorts in Lanesborough ](https://www.expedia.com/Lanesborough-Resorts.d6005408-aaResorts.Travel-Guide-Accommodation) - [Motels in Lanesborough ](https://www.expedia.com/Lanesborough-Motels.d6005408-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Lanesborough ](https://www.expedia.com/Lanesborough-Apart-Hotels.d6005408-aaApartHotels.Travel-Guide-Accommodation) - [Condo Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Condos.d6005408-aaCondos.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough ](https://www.expedia.com/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Motels in New Ashford ](https://www.expedia.com/New-Ashford-Motels.d183333-aaMotels.Travel-Guide-Accommodation) - [Apartments in New Ashford ](https://www.expedia.com/New-Ashford-Apartments.d183333-aaApartments.Travel-Guide-Accommodation) - [B&B in New Ashford ](https://www.expedia.com/New-Ashford-Bed-And-Breakfast.d183333-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Vacation Homes in New Ashford ](https://www.expedia.com/New-Ashford-Private-Vacation-Homes.d183333-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Lanesborough Hotels ](https://www.expedia.com/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [Cheap Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Luxury-Hotel.0-0-d6005408-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Ski Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Ski-Hotel.0-0-d6005408-tSkiHotel.Travel-Guide-Filter-Hotels) - [B&B in Adams ](https://www.expedia.com/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Apartments in Adams ](https://www.expedia.com/Adams-Apartments.d6005393-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Adams ](https://www.expedia.com/Adams-Cabins.d6005393-aaCabins.Travel-Guide-Accommodation) - [Cottages in Adams ](https://www.expedia.com/Adams-Cottages.d6005393-aaCottages.Travel-Guide-Accommodation) - [Motels in Adams ](https://www.expedia.com/Adams-Motels.d6005393-aaMotels.Travel-Guide-Accommodation) - [Resorts in Adams ](https://www.expedia.com/Adams-Resorts.d6005393-aaResorts.Travel-Guide-Accommodation) - [Condo Rentals in Adams ](https://www.expedia.com/Adams-Condos.d6005393-aaCondos.Travel-Guide-Accommodation) - [Hotels near Susan B. 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