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Top Mountain Massachusetts Hotels

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

₩278,285

₩310,844 total

Mar 8 - Mar 9

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 ...

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 Oct 5, 2025

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 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

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Chambery Inn

199 Main St Lee MA

30 min drive from Fenway Park

Stay at this B&B in Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Berkshire Mountain Country Store and Animagic Museum of ...

9.4/10 Exceptional! (374 reviews)

We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew ...

Reviewed on Nov 3, 2025

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See all 17,767 properties in Massachusetts

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.