Title: Mountain Vacations in Western Massachusetts 2026 | Expedia.ca ![](https://images.trvl-media.com/place/95847/112792fe-fb09-4a78-9e92-4c8f980ab208.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Western Massachusetts Mountain Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Tu Nguyen - ## 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 ## 4 Night Mountain holidays in Western Massachusetts Price found within the past 48 hours. Click for updated prices. ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Vacation Village in the Berkshires CA $942 per person Mar 16 - Mar 20 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 8.8/10 Excellent! (2,134 reviews) Clean rooms, chimney did not work Reviewed on Jan 4, 2026 ![Cavalier Cottage B&B](https://images.trvl-media.com/lodging/19000000/18620000/18610500/18610415/e20cf265_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Cottage B&B CA $1,190 per person Mar 16 - Mar 20 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Boston (BOS) 9/10 Wonderful! (2 reviews) ![1896 House Country Inn & Motels](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ed652faf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1896 House Country Inn & Motels CA $987 per person Mar 16 - Mar 20 found 10 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Albany (ALB) 6.6/10 (448 reviews) The price is good. It's a classic motel from the '50's, but gets the job done. Reviewed on Oct 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Western Massachusetts [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-11/2026-02-18/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=HFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Mountain Hotels in Western Massachusetts ![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 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 ... 8.2/10 Very Good! (988 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 - 3 min walk from Jiminy Peak Mountain Resort 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! (566 reviews) The sound proof is a problem Reviewed on Jan 5, 2026 [](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/e20cf265_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cavalier Cottage B&B 236 East Oxbow Road Shelburne Falls MA - 21 min drive from Jiminy Peak Mountain Resort Stay at this 3-star business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free WiFi, 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 Apr 13, 2018 [](https://expedia.ca/Shelburne-Falls-Hotels-Cavalier-Cottage-BB.h18610415.Hotel-Information) [See all 1,472 properties in Western Massachusetts](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=6234063) 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 Western Massachusetts ](https://expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)[ Western Massachusetts Hotels ](https://expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels)[ Western Massachusetts Vacation Rentals ](https://expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)[ Western Massachusetts Car Rentals ](https://expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)[ Western Massachusetts Vacations ](https://expedia.ca/Western-Massachusetts.d6234063.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