
Massachusetts Mountain Vacations
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Top Mountain Massachusetts Hotels

Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
The price is ¥21,278 per night from Oct 26 to Oct 27
¥21,278
¥23,767 total
Oct 26 - Oct 27
includes taxes & fees
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

Cavalier Cottage B&B
236 East Oxbow Road, Shelburne Falls, MA
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

Harbour House Inn
725 North State Road, Cheshire, MA
The price is ¥39,846 per night from Oct 30 to Oct 31
¥39,846
¥42,117 total
Oct 30 - Oct 31
includes taxes & fees
Stay at this 3.5-star B&B in Cheshire. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation ...
9.6/10 Exceptional! (38 reviews)
The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people.
Reviewed on Sep 12, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
