Massachusetts Mountain Vacations
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Top Mountain Massachusetts Hotels
Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
The price is ₩220,692 per night from Sep 1 to Sep 2
₩220,692
₩246,513 total
Sep 1 - Sep 2
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! (962 reviews)
Good base to do things in the Berkshires
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
Reviewed on Aug 11, 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
Chambery Inn
199 Main St, Lee, MA
The price is ₩312,286 per night from Sep 18 to Sep 19
₩312,286
₩348,818 total
Sep 18 - Sep 19
includes taxes & fees
Stay at this 3-star B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Tanglewood Music Center and Berkshire Mountain ...
9.4/10 Exceptional! (368 reviews)
"Beautiful stay. We booked last minute and it was amazing! We were able to book the room with jacuzzi and a fireplace—which made the whole stay so romantic. Will recommend and am planning to visit regularly. Hoping to return in the fall but definitely next spring. This family works hard and takes ..."
Reviewed on Jun 13, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.