Title: Cheshire Condo Rentals from CA $126 | 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 # Search Condos Rentals in Cheshire from CA $126 ![](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 [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 two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-14&endDate=2025-11-16&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire Condo Rentals ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.8/10 Excellent (2112) "Great place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $99 CA $126 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1080h783x0y5-9ee375ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/a814c17c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/c54967a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### UNIQUE - 1BR Country Condo @ Jiminy Peak Hancock 10/10 Exceptional (14) "Clean and quiet, nicely decorated! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $180 CA $484 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/34492d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/82468102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/a111c8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/7e1d3e97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7 Hancock 8.0/10 Very good (8) "Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sam R. CA $191 CA $469 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/266e4752.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/d5e215b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/1b985d8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/b6c32865.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous Hancock 9.0/10 Wonderful (2) "very nice and roomy! really enjoyed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shack M. CA $191 CA $421 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.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=2025-11-12&endDate=2025-11-13®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-Condos.d6005398-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Condos.d6005398-aaCondos.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Excellent all the way around" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "Good location; reasonable price; very clean and quiet - would definitely return" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "Everything is clean " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 "Very clean and roomy lodge (2 bedrooms); conveniently located; has kitchen; recreational facilities a bit dated. Will come back again. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "I have stayed here many times and it is consistently a comfortable, clean and quiet place." [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 "View of the lake was lovely! Breakfast was fine—yogurt, eggs, pancakes and cereal. Coffee was plentiful!" [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Lovely property, friendly, helpful staff. Modern, large rooms. Pretty decor." [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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 "Great place. Friendly staff and very well located. Great breakfast options. " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![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) ## Find out more about Cheshire ## Cheshire Condo Rentals information | Number of reviews | 2,126 | | --- | --- | | Accommodation | 64 Condo Rentals | | Lowest Price | CA $126 | | Highest Price | CA $484 | ## Frequently asked questions ### How much do condos in Cheshire cost? > Condos in Cheshire range from CA $126 to CA $484 per night. This will give you loads of room for your whole crew at a price that fits your budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply. ### How many condos are there in Cheshire? > There are 64 condos in Cheshire. Whether you're taking a trip with the little ones or organizing a weekend break with some friends, Expedia will help you find the perfect space for your squad. ### Are there any family-friendly condos in Cheshire? > If you're planning an escape in Cheshire and after a family-friendly condo, we recommend [Vacation Village In The Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information). This 3-star stay offers a garden and a swimming pool. After checking in and chilling out in your comfortable new digs, it's time to visit some of the local sights. [Jiminy Peak Mountain Resort](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.Vacation-Attraction) and [Mount Greylock](https://www.expedia.ca/Mount-Greylock-Adams.d6091829.Vacation-Attraction) are just two family-friendly attractions in Cheshire. ### Why book your condo in Cheshire with Expedia? > We think that vacations should be stress-free, so if you're seeking condos at a competitive rate, Expedia can help. Keep the budget under control and choose something small and affordable, or book a 5-star condo and spoil the ones you love most. Use our convenient search filters to find a stay in Cheshire that matches your needs. ### How can I find cheap condos in Cheshire? > Expedia can help you easily source cheap condos in Cheshire. To discover your perfect stay in just a few keystrokes, simply use our convenient filter tool to refine your search results by star rating, budget and amenities. ### What is there to do in Cheshire near my condo? > The most useful travel accessory is a well-planned to-do list. [St Mary's of the Assumption Church](https://www.expedia.ca/St-Marys-Of-The-Assumption-Church-Cheshire.d553248621532665539.Vacation-Attraction) is a wonderful place to kick off your adventures in Cheshire. ## 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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