Title: The Berkshires Condo Rentals | Expedia.ca [The Berkshires Travel Guide](https://expedia.ca/The-Berkshires.dx6047665)[Hotels in The Berkshires](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[Vacation Rentals in The Berkshires](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacation Packages](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) ![The Berkshires showing snow and snowboarding](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/71000/71823-The-Berkshires.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Condos Rentals in The Berkshires ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select The Berkshires 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) ![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) ![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) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2045) "Easy check in and out, clean room. " CA $128 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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) ![Exterior](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/7e1d3e97.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111670000/111663300/111663271/d1c43c74.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" CA $190 CA $464 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Condo-Mountain-Views-At-Jiminy-Peak-Sleeps-7.h111663271.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) ![Interior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h808x0y2-de6afae7.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) ![Exterior](https://images.trvl-media.com/lodging/75000000/74320000/74312900/74312811/w1075h806x0y5-6945b1ad.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! " CA $180 CA $486 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Hancock-Hotels-UNIQUE-Gnome-Themed-1BR-Condo.h74312811.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/d5e215b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/7e179971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/cdf98da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/119000000/118090000/118080600/118080540/w911h606x0y0-40def80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous Hancock 8.0/10 Very good (1) "very nice and roomy! really enjoyed." CA $190 CA $418 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Hancock-Hotels-2-BR-Jiminy-Peak-W-Mountain-View-Sleeps-7-Gorgeous.h118080540.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/cdd47fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/a569d1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/f081e4c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, toilet paper](https://images.trvl-media.com/lodging/116000000/115670000/115661000/115660983/00b27946.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom condo in delightful Dover Dover 9.0/10 Wonderful (4) "Condo was perfect for our stay. Very quiet area despite being near Mt Snow and Wilmington area. Great bakery close by for wonderful morning pastries. Updated/renovated condo. Loved our time there. Owners response to an issue we had (our personal issue) was greatly appreciated. Would stay again!!!!" CA $149 CA $282 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/West-Dover-Hotels-Charming-1-Bedroom-Condo-In-Delightful-Dover.h115660983.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/110000000/109530000/109523700/109523693/18e29102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109530000/109523700/109523693/177f68b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109530000/109523700/109523693/dc09a805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/110000000/109530000/109523700/109523693/7fb4bc1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 3-bedroom condo in serene Wilmington - Your home away from home! Wilmington 10/10 Exceptional (1) "Beautiful condo that is spacious in a quiet spot" CA $502 CA $906 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Wilmington-Hotels-Charming-3-Bedroom-Condo-In-Serene-Wilmington-Your-Home-Away-From-Home.h109523693.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/c941b5c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/1d62c6d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/6839e531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/89000000/88640000/88639400/88639305/fce63aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities Dover 8.6/10 Excellent (31) "The apartment was in a great location to get to the ski lifts. " CA $109 CA $398 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/West-Dover-Hotels-Ski-Inski-Out-Condo-With-Deck.h88639305.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/32130af3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/537d56ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/5bf866db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/49000000/48190000/48188500/48188407/6f40afa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 3 bedroom condo 2.5 miles to Mount Snow West Dover 9.0/10 Wonderful (42) "This is the third time I’ve stayed here and it’s very convenient and I really love what the host did for upgrades on the property. " CA $126 CA $410 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h48188407.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89400000/89393600/89393580/8abfda69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi](https://images.trvl-media.com/lodging/90000000/89400000/89393600/89393580/b083eef4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/90000000/89400000/89393600/89393580/4a04c8d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89400000/89393600/89393580/58b14015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat) Dover 9.4/10 Exceptional (18) "Clean, comfortable, convenient! " CA $405 CA $960 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/West-Dover-Hotels-Family-Mount-Snow-Condo-4-Mins-Walk-From-Sundance-Lift.h89393580.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/113670000/113669700/113669647/98816620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113670000/113669700/113669647/6c2cd4bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113670000/113669700/113669647/1caf4b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/114000000/113670000/113669700/113669647/7f1a0683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2BR Loft With Views | Ski-In Access West Dover CA $603 CA $750 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/West-Dover-Hotels-2BR-Loft-With-Views-Ski-In-Access.h113669647.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=2025-10-23&endDate=2025-10-24®ionId=6047665&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%2FThe-Berkshires-Condos.d6047665-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Condos.d6047665-aaCondos.Travel-Guide-Accommodation) ## Top The Berkshires Hotel Reviews ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Easy parking, great community spaces, beautiful decor! " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Great lodge with 1 bedroom suites and fully stocked kitchens " [](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 "Clean room. Spacious with lovely things to do. " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.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 "This is a fun family resort... a great vacation place .. in a great location.. something for everyone. Perfect family reunion place.. All Ages happy.. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Nice place to stay for a wedding " [](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 location, very clean!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Brand new property with friendly and helpful people." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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 "Room was clean & comfortable. Thank you! Parking was kind of far." [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Jiminy Peak Mountain Resort](//images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg) ### Jiminy Peak Mountain Resort 10/10 Excellent "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." [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ## Find out more about The Berkshires ## The Berkshires Condo Rentals information | Number of reviews | | | --- | --- | | Accommodation | Condo Rentals | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### How much do condos in The Berkshires cost? > The price range for condos in The Berkshires is to per night. No matter your budget, you'll find someplace that suits your needs — as well as your entire squad! 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 The Berkshires? > Explore our condos in The Berkshires and then select your favorite. Whether you're embarking on a vacation with all the fam or kicking it with friends, your perfect stay is just clicks away. ### Why book your condo in The Berkshires with Expedia? > Reserving a condo in The Berkshires is as easy as entering your travel dates and choosing a place that has what you need. On the lookout for something low cost or luxurious, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results even further and find the perfect pad. ### How can I find cheap condos in The Berkshires? > The quickest way to score cheap condos in The Berkshires is with Expedia's easy-to-use filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks. ### What is there to do in The Berkshires near my condo? > Whether you enjoy arts, culture, shopping or dining, The Berkshires offers the lot, and then some! The awesome city of Lenox boasts plenty of things to do and see, including [Tanglewood Music Center](https://www.expedia.ca/Tanglewood-Music-Center-Lenox.d503292.Vacation-Attraction), [Shakespeare and Company](https://www.expedia.ca/Shakespeare-And-Company-Lenox.d6127086.Vacation-Attraction) and [The Mount](https://www.expedia.ca/The-Mount-Lenox.d553248621532665265.Vacation-Attraction). If you're planning an escape to Williamstown, [Chapin Library of Rare Books and Manuscripts](https://www.expedia.ca/Chapin-Library-Of-Rare-Books-And-Manuscripts-Williamstown.d553248621532665544.Vacation-Attraction), [Hopkins Observatory](https://www.expedia.ca/Hopkins-Observatory-Williamstown.d6091831.Vacation-Attraction) and [Williams College Museum of Art](https://www.expedia.ca/Williams-College-Museum-Of-Art-Williamstown.d6091837.Vacation-Attraction) are must-do's. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Boutique-Hotel.0-0-d110336-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Cheap-Hotels.0-0-d110336-tCheapHotels.Travel-Guide-Filter-Hotels) - 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