Western Massachusetts Mountain Holidays

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Photo by Photo courtesy of Berkshire Visitors Bureau
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Top Mountain Western Massachusetts Hotels

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
  • 1 hour drive from Six Flags New England
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 bars/lounges. Our guests praise the property condition in their reviews. Popular ...
8.2/10 Very Good! (943 reviews)
"Beautiful setting. Friendly staff."

Reviewed on 30 Jun 2025

Jiminy Peak Mountain Resort
Club Wyndham Bentley Brook
Club Wyndham Bentley Brook
3 out of 5
1 Corey Road, Hancock, MA
  • 1 hour drive from Six Flags New England
Stay at this 3-star ski hotel in Hancock. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (527 reviews)
"Really nice modern units and layout. Loved the car charger for our EV. We stayed in and cooked, as there were minimal food options in the area. Lovely stay and we will be back!"

Reviewed on 7 Jun 2025

Club Wyndham Bentley Brook
Cavalier Cottage B&B
Cavalier Cottage B&B
3 out of 5
236 East Oxbow Road, Shelburne Falls, MA
  • 2 hours drive from Six Flags New England
Stay at this 3-star business-friendly cottage in Shelburne Falls. Enjoy free breakfast, free Wi-Fi 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 13 Apr 2018

Cavalier Cottage B&B
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.