Title: Cheshire Inns from CA $158 | 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) ![](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 prices for these dates Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=INN&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Cheshire inns ![Dining room](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/595e173f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/920e0060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/36309153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/111000000/110080000/110070300/110070215/14f6a8c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gregory House Country Inn [](https://www.expedia.ca/Averill-Park-Hotels-Gregory-House-Country-Inn.h110070215.Hotel-Information) Averill Park 9.0/10 Wonderful (91 reviews) "Loved the fact that we could have dinner and Sunday brunch right there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maureen CA $142 CA $158 total includes taxes & fees Apr 4 - Apr 5 [](https://www.expedia.ca/Averill-Park-Hotels-Gregory-House-Country-Inn.h110070215.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/126000000/125080000/125075000/125074901/9b85b992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/126000000/125080000/125075000/125074901/95cf3b4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Loft, 1 King Bed, Mountain View](https://images.trvl-media.com/lodging/126000000/125080000/125075000/125074901/8cf48229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Loft, 1 King Bed, Mountain View](https://images.trvl-media.com/lodging/126000000/125080000/125075000/125074901/7a3f6dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hideaway Inn Lenox [](https://www.expedia.ca/Lenox-Hotels-Hideaway-Inn-Lenox.h125074901.Hotel-Information) Lenox CA $214 CA $239 total includes taxes & fees Mar 31 - Apr 1 [](https://www.expedia.ca/Lenox-Hotels-Hideaway-Inn-Lenox.h125074901.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/39fc54d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/54079ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/68872253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/b07cfd29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) Williamstown 6.6/10 (449 reviews) "Place was convenient, cleaned and quiet a little old, but all in all a good stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelley [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.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=2026-04-07&endDate=2026-04-08®ionId=6005398&adults=2&lodging=INN&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-Inns.d6005398-aaInns.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Inns.d6005398-aaInns.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "very clean and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 10/10 Excellent "Great, neat, convoy my son. " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Great place to enjoy with the whole family!!!" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072_y.jpg) ### The Porches Inn at Mass MoCA 8/10 Good "It was a great stay at a place that was a cut above the usual hotel stay. Breakfast was provided but we only ate there 1 day for we wanted to experience things away from the place. There are many delicious places to eat for breakfast so try it. The location was perfect allowing for walking around whether to MOCA or finding other shops. While we didn’t bring our dog along this time, perhaps we will next time. " [](https://expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.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 "Staff was pleasant! Clean and the restaurant was excellent!" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 10/10 Excellent "Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The exercise room is small. Not crowded. The pool was in use most of the time we were there as the pool is used for children's swimming lessons. We didn't want to use the hot tub with a bunch of kids and parents splashing around. Good staff and very responsive. " [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Completely comfortable. Excellent restaurant. " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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 "Goodnight " [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg) ### The Whitlock 10/10 Excellent "The facility is unfortunately only staffed 2-8pm daily. None of exterior doors lock at night. Front desk staff was very helpful. The place was very clean and convenient to shops and restaurants." [](https://expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ## Find out more about Cheshire ## Cheshire Inns information | Number of reviews | 91 | | ----------------- | ------- | | Accommodation | 5 Inns | | Lowest Price | CA $158 | | Highest Price | CA $239 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in North Adams ](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [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) - [Guest Houses in Adams ](https://www.expedia.ca/Adams-Guest-Houses.d6005393-aaGuestHouses.Travel-Guide-Accommodation) - 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