Title: Mountain Vacations in Massachusetts 2026 | Expedia.ca ![](https://images.trvl-media.com/place/223/15b716aa-7bcd-4985-a9a4-b76daf9495af.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Massachusetts Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Massachusetts ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jiminy Peak Mountain Resort 37 Corey Rd Hancock MA CA $207 CA $231 total Apr 1 - Apr 2 includes taxes & fees Book a stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 hot tubs. Our guests praise the property condition in our reviews. Popular ... [](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/f968e782_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Wyndham Bentley Brook 1 Corey Road Hancock MA Book a stay at this 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! (569 reviews) The sound proof is a problem Reviewed on Jan 5, 2026 [Get rates](https://expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) [](https://expedia.ca/Hancock-Hotels-Club-Wyndham-Bentley-Brook.h973618.Hotel-Information) ![Cavalier Cottage B&B](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/c9ff5b19_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 Book a stay at this business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Catamount State Forest ... [Get rates](https://expedia.ca/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) [](https://expedia.ca/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) [See all 17,968 properties in Massachusetts](https://expedia.ca/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 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 [Massachusetts Flights ](https://expedia.ca/Destinations-In-Massachusetts.d223.Flight-Destinations)[ Massachusetts Hotels ](https://expedia.ca/Destinations-In-Massachusetts.d223.Hotel-Destinations)[ Massachusetts Vacation Rentals ](https://expedia.ca/Destinations-In-Massachusetts.d223.Vacation-Rental-Destinations)[ Massachusetts Car Rentals ](https://expedia.ca/Destinations-In-Massachusetts.d223.Car-Rental-Destinations)[ Massachusetts Vacations ](https://expedia.ca/Massachusetts.d223.Destination-Travel-Guides)[ Things to do in Massachusetts ](https://expedia.ca/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. ![](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