Title: The Berkshires Villas from CA $1,039 | 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 which includes flowers](https://images.trvl-media.com/place/6047665/e95ad08c-cd3f-48ea-b01c-31171bbd50b7.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Photo courtesy of Berkshire Visitors Bureau # Search The Berkshires Villa Rentals from CA $1,039 - ![](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 In two weeks [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6047665&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=6047665&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) ## Our top choices for The Berkshires villas ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/79e104d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/7a56f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/fc7d25b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Whately [](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information) 10/10 Exceptional (8) "Thanks for a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea M. CA $824 CA $1,039 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102750000/102743000/102742957/56070e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102750000/102743000/102742957/562a8a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102750000/102743000/102742957/29e1c7a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102750000/102743000/102742957/ed909360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Pownal [](https://www.expedia.ca/Pownal-Hotels-Vermont-Vacation-VillaGrapevine-Getaway.h102742957.Hotel-Information) 9.4/10 Exceptional (3) "The villa was great! The house is very spacious and clean. We really enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jenna S. CA $575 CA $1,200 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Pownal-Hotels-Vermont-Vacation-VillaGrapevine-Getaway.h102742957.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=2026-01-18&endDate=2026-01-19®ionId=6047665&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.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=CABIN) Chalets [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=CHALET) Cottages [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=VACATION_HOME) Apartments [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=APART_HOTEL) Condos [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=The+Berkshires%2C+Massachusetts%2C+United+States+of+America®ionId=6047665&latLong=42.166802%2C-73.149597&adults=2&startDate=2026-04-04&d1=2026-04-04&endDate=2026-04-07&d2=2026-04-07&lodging=VILLA) ![](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-Villas.d6047665-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Villas.d6047665-aaVillas.Travel-Guide-Accommodation) ## Top The Berkshires Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Nice warm pool and hot tub. Good little fitness center. " [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "The rooms are clean, the pool is nice and the location is perfect for Jiminy Peak! " [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "We chose this location for our family Christmas getaway because the amenities looked appealing and the price was affordable—and we were more than pleased with our three-night stay. The property is incredibly family-friendly. The pool and arcade had great hours, and while the arcade was small, it offered a fun selection of games. The pool and outdoor hot tub were kept at perfect temperatures, and even when busy, there was plenty of space for everyone. Relaxing in the hot tub during a snowstorm was one of the highlights of our trip. Each night, the common room hosted a movie night, which was wonderful to see families come together and enjoy time as a group. The front desk also offered DVD and game rentals, and it was refreshing to see families playing classic board games and laughing together—a pastime that seems rare these days. The lobby and common areas were spacious and cozy, especially with the warm fireplaces, where our family spent a few hours each evenings playing games. Our suite was roomy, comfortable, and felt like home. The well-stocked kitchen was a bonus. The staff was friendly and accommodating, and having a Stop & Shop directly across the street was incredibly convenient. We are more than pleased with this establishment and would both recommend and return for another family getaway! " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg) ### Prospect Berkshires 10/10 Excellent "Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!" [](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Clean room | Staff " [](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "The stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 "Did not have breakfast. Wish it was free but the hotel staff was amazing and the valet was great too! " [](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](https://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 "We had a great stay! Karaoke in the bar was a blast!! Great little condo!!" [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Staff were very friendly and flexible. The rooms were comfortable, spacious and clean. Easy checking and checking out. Plenty of parking. Would definitely stay there again and again. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Find out more about The Berkshires ## The Berkshires Villas information | Number of reviews | 10 | | ----------------- | --------- | | Accommodation | 1 Villas | | Lowest Price | CA $1,039 | | Highest Price | CA $1,200 | ## Frequently asked questions ### How much do villas in The Berkshires cost? ### Why book your villa in The Berkshires with Expedia? ### How can I find cheap villas in The Berkshires? ### What is there to do near my villa in The Berkshires? ## 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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