Title: The Berkshires Mountain Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/6047665/bda2c66e-c12e-41fa-bcf4-6a6872be8f56.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Berkshires Mountain Holidays ## Book a Mountain Hotel + Flight or Car together to unlock savings Photo by Photo courtesy of Berkshire Visitors Bureau - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ## Top Mountain The Berkshires Hotels ![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 - 4 min walk from Jiminy Peak Mountain Resort Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ... 8.2/10 Very Good! (987 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 5 Oct 2025 [](https://expedia.co.uk/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 - 3 min walk from Jiminy Peak Mountain Resort Stay at this ski hotel in Hancock. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the property condition ... 9.2/10 Wonderful! (565 reviews) Cleanliness Reviewed on 9 Dec 2025 [](https://expedia.co.uk/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 - 41 min drive from Jiminy Peak Mountain Resort Stay at this B&B in Lee. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Berkshire Mountain Country Store and Animagic Museum of ... 9.4/10 Exceptional! (373 reviews) We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew ... Reviewed on 3 Nov 2025 [](https://expedia.co.uk/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) [See all 1,084 properties in The Berkshires](https://expedia.co.uk/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 holidays 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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## More Holiday Ideas [Flights to The Berkshires ](https://expedia.co.uk/Cheap-Flights-To-The-Berkshires.d6047665.Travel-Guide-Flights)[ The Berkshires Hotels ](https://expedia.co.uk/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)[ The Berkshires Holiday Rentals ](https://expedia.co.uk/The-Berkshires-Holiday-Rentals.d6047665.Travel-Guide-HolidayRentals)[ The Berkshires Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Berkshires.d6047665.Car-Hire-Guide)[ The Berkshires Holidays ](https://expedia.co.uk/The-Berkshires.d6047665.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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