Title: Cheshire Condominium Resort Rental from CA $188 | 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) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find and Compare Cheshire Condo Resort Rentals ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire Condo Resorts ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/662f1ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Bedroom Condo 1/2 mile from base | In-room dining](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/40940c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jiminy Peak Mountain Resort Hancock 8.2/10 Very good (984) "This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $196 CA $219 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/eda478dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f251fc45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/f5477a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ponds at Foxhollow Lenox 8.6/10 Excellent (132) "We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle CA $168 CA $188 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.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=2025-11-08&endDate=2025-11-09®ionId=6005398&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-Condominium-Resort.d6005398-aaCondominiumResort.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Condominium-Resort.d6005398-aaCondominiumResort.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Clean room" [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "An amazing service the staff is very friendly and helpful, it’s a nice location and a great place " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Vacation Village in the Berkshires](//images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Check in was easy. Room was clean and well-stocked. Lay out for the double room was great. Pool was well-maintained. Game room was added benefit. Very nice stay." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 10/10 Excellent "This motel is an original from the 50's or 60's. I would not say it has been renovated, it has been updated and merticusly maintained over the years. The ambience is truly retro. In an instant I recognized this is a loved family owned property." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Good value. A good place." [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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 10/10 Excellent "Our room was clean as a pin and we loved the option of daily maid service. Love that there’s a closet with adequate hangers, extra blanket, clock, and the shampoo, body wash dispensers in the shower. Towels were big and fluffy. LOVE the heat lamp in the bathroom!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean room " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Had a lovely stay at the Berkshires Untold! We checked in late and the staff reached out to confirm our arrival time and accommodated us without issue. The lobby was absolutely gorgeous and this renovated motel was very well done. We didn’t get to enjoy the fire pits outside but they looked cozy. We also did not have any food or beverage. The room was perfect for two of us, had all the basic amenities and was charming. Overall had a very pleasant stay! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "All was very good at this hotel, our room was modernized and updated. The people at the front desk as well as all the employees were all well trained and pleasant . Pittsfield is in the middle of The Berkshires and so it was a great location to see what we wanted to see. " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ## Find out more about Cheshire ## Cheshire Condo Resorts information | Number of reviews | 1,116 | | --- | --- | | Accommodation | 2 Condo Resorts | | Lowest Price | CA $188 | | Highest Price | CA $219 | ## 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) - 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