Title: Mountain Vacations in The Berkshires 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Photo courtesy of Berkshire Visitors Bureau Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 when you book a flight and hotel together\* ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package ### Rest easy Plan, book, and manage your trip all in one place ## Mountain Hotels in The Berkshires ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd, Hancock, MA - 34 min drive from Tanglewood Music Center Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ... 8.2/10 Very Good! (982 reviews) 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 ... Reviewed on Oct 5, 2025 [](https://expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Club Wyndham Bentley Brook](https://images.trvl-media.com/lodging/1000000/980000/973700/973618/bb582c2d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Wyndham Bentley Brook 1 Corey Road, Hancock, MA - 34 min drive from Tanglewood Music Center Stay at this 3-star ski hotel in Hancock. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the property condition ... 9.2/10 Wonderful! (550 reviews) quiet and clean Reviewed on Oct 16, 2025 [](https://expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) ![Chambery Inn](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chambery Inn 199 Main St, Lee, MA - 8 min drive from Tanglewood Music Center Stay at this 3-star B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ... 9.4/10 Exceptional! (369 reviews) ease of late check in. Super comfortable room. Reviewed on Aug 24, 2025 [](https://expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) [See all 1,102 properties in The Berkshires](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6047665) 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. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## More Vacations Ideas [Flights to The Berkshires](https://expedia.ca/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[The Berkshires Hotels](https://expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[The Berkshires Vacation Rentals](https://expedia.ca/The-Berkshires-Vacation-Rentals.d6047665.Travel-Guide-VacationRentals)[The Berkshires Car Rentals](https://expedia.ca/Car-Rentals-In-The-Berkshires.d6047665.Car-Rental-Guide)[The Berkshires Vacations](https://expedia.ca/The-Berkshires.d6047665.Destination-Travel-Guides) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)