Massachusetts Ski Vacations

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Top Ski Massachusetts Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
  • 8 min walk from Fenway Park
The price is ¥16,200 per night from Dec 16 to Dec 17
¥16,200
¥19,804 total
Dec 16 - Dec 17
includes taxes & fees
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,169 reviews)
Your staff is very courteous and yes my room was spotless.

Reviewed on Dec 13, 2025

Vacation Village in the Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
  • 13 min drive from Fenway Park
The price is ¥12,317 per night from Dec 24 to Dec 25
¥12,317
¥13,758 total
Dec 24 - Dec 25
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,002 reviews)
The room was fantastic, cozy as can be! Also, as soon as you walk into the lobby it looked wonderful! The Manager, Jennifer was so nice to talk too! She made sure everything with room, etc. was good! She was a delight!

Reviewed on Dec 12, 2025

The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd Williamstown MA
  • 14 min drive from Fenway Park
The price is ¥19,492 per night from Jan 4 to Jan 5
¥19,492
¥21,773 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this hotel in Williamstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (564 reviews)
We had a short but pleasant stay.

Reviewed on Sep 30, 2025

Berkshire Valley Inn
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.