Title: Massachusetts Mountain Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/223/15b716aa-7bcd-4985-a9a4-b76daf9495af.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Massachusetts Mountain Holidays ## Book a Mountain Hotel + Flight or Car together to unlock savings - ## 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 Massachusetts 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 £155 8 Mar - 9 Mar includes taxes & fees 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! (989 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 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! (568 reviews) The sound proof is a problem Reviewed on 5 Jan 2026 [Get rates](https://expedia.co.uk/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) [](https://expedia.co.uk/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) ![Cavalier Cottage B&B](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/e20cf265_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cavalier Cottage B&B 236 East Oxbow Road Shelburne Falls MA - 35 min drive from Fenway Park Stay at this 3-star business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Catamount State Forest ... Would return! Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor ... Reviewed on 13 Apr 2018 [Get rates](https://expedia.co.uk/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) [](https://expedia.co.uk/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) [See all 17,713 properties in Massachusetts](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=223) 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 [Massachusetts Flights ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Flight-Destinations)[ Massachusetts Hotels ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Hotel-Destinations)[ Massachusetts Holiday Rentals ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Holiday-Rental-Destinations)[ Massachusetts Car Hire ](https://expedia.co.uk/Destinations-In-Massachusetts.d223.Car-Hire-Destinations)[ Massachusetts Holidays ](https://expedia.co.uk/Massachusetts.d223.Holidays-City-Breaks)[ Things to do in Massachusetts ](https://expedia.co.uk/Things-To-Do-In-Massachusetts.d223.Travel-Guide-Activities) \* 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