Title: The Berkshires Chalets | 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 Chalets in The Berkshires - ![](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 [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6047665&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 [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 three 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) In four 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) ## Browse Select The Berkshires Chalets ![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/14b70d1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/c26da9c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/083f8263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/163b8b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow West Dover 10/10 Exceptional (20) "great space for adults and teenagers. loved the hot tub! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica M. CA $252 CA $857 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/6eef057c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/d3aa8c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/2d0f8d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/e32ae717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vikings Villages Resort - Double Bed Room Guilford CA $386 CA $517 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/89954d4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/7665cd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/36af79f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36780000/36777700/36777699/c71f56f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House Dover 9.8/10 Exceptional (22) "Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SZU YIN C. CA $118 CA $572 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/West-Dover-Hotels-MT-SNOW-SKI-BACK-TRAIL-FREE-SHUTTLE-Green-Mountain-House.h36777699.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/dfb0d0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Chalet mins from Mt Snow Skiing/hiking East Dover 9.8/10 Exceptional (9) "Easy to find! Clean! Cozy!! Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roy-michael G. CA $164 CA $612 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/83acf129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/cc65421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/fc99bbc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/106000000/105990000/105982900/105982869/7b2fb729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private cabin: 7 mins to slopes, wood fireplace Dover 9.6/10 Exceptional (5) "Had a lovely stay here in mid-August. Despite the rain, played two rounds of golf at the beautiful resorts at Mt. Snow and Stratton. The house is nestled in the woods with a great view of the mountain ski trails. House is very spacious and the kitchen has everything you need! Our only issue was the lack of AC. Our bad luck to pick the most humid weekend of the summer, I guess, bc I know AC is rare in VT but maybe add more ceiling fans? Aside from that, we had a great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne H. CA $246 CA $787 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/West-Dover-Hotels-Mountain-View-Chalet-Golf.h105982869.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1071x0y2-62744863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y0-ad90e439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, foosball, books](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/84b8211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112680000/112675200/112675182/w1080h1076x0y4-eec2a42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub! Dover 10/10 Exceptional (4) "We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris I. CA $445 CA $982 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/West-Dover-Hotels-Gorgeous-4-Bedroom-3-Bath-Chalet-In-Dover-10-Minutes-To-Mount-Snow-WIFI.h112675182.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/76d2f10f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/bfdbff3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/f9ad7feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109560000/109550900/109550875/accd446a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus Dover 10/10 Exceptional (8) "Get together with old friends. Had an easy time checking in and a great time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erik D. CA $252 CA $948 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Hot-Tub.h109550875.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2392h1338x0y2-be276e7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/97a2d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/w2180h1456x4y0-3d3ff46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110990000/110980800/110980715/e95e3631.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Private Chalet - 4 mins to Mt Snow Dover 10/10 Exceptional (1) CA $253 CA $816 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/West-Dover-Hotels-NEW-Private-Chalet-4-Mins-To-Mt-Snow.h110980715.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/5f637af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/130b5998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/9a7f483c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/79000000/78500000/78494300/78494299/4c3f61c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Chalet w. Hot Tub - 1 mile to Mt. Snow Dover 10/10 Exceptional (14) "The Chalet was perfect for my families stay in Vermont. We spent the week hiking, exploring the waterfalls and all the towns. The house had everything we needed after a day of hiking. All the games were great too. The house was very clean and well maintained. Thank you for allowing us to stay at The Chalet!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John S. CA $420 CA $1,000 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/West-Dover-Hotels-Charming-Chalet-W-Hot-Tub-1-Mile-To-Mt-Snow.h78494299.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=2025-11-23&endDate=2025-11-24®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-Chalets.d6047665-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FThe-Berkshires-Chalets.d6047665-aaChalets.Travel-Guide-Accommodation) ## Top The Berkshires Hotel Reviews ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "I love the ambience - historic and comfortable and excellent food. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](//images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "I had a smooth check in. A little later I went back to the front desk to get an extra key, was asked my room number and last name. The associate, knew that I had asked for extra pillows when I made the reservation. I don't think he was even on my reservation on the computer yet to see the note. Asked if I had the extra pillows in the room and were they ok! Often hotels don't even notice this request, never mind remember it or ask about it. Great attention to details!" [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 "Everything was fine just no shampoo in the dispencer" [](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Great staff and the room was awesome!! Would definitely come again!" [](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 "Spotless and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you" [](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 "The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more." [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ## Find out more about The Berkshires ## The Berkshires Chalets information | Number of reviews | | | --- | --- | | Accommodation | Chalets | | Lowest Price | | | Highest Price | | ## 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) - [Hotels with a Pool in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Hotel-With-Pool.0-0-d110336-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Hotels-With-Hot-Tubs.0-0-d110336-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - 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