Compare Ski Hotels in Western Massachusetts
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Check hotel availability in Western Massachusetts
Tomorrow night
Check prices in Western Massachusetts for tomorrow night, 19 Dec - 20 DecFeatured Western Massachusetts Ski Hotels
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is NZ$220 per night from 4 Jan to 5 Jan
NZ$220
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$183 per night from 21 Dec to 22 Dec
NZ$183
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Berkshire Valley Inn
2541 Hancock Rd Williamstown MA
The price is NZ$242 per night from 4 Jan to 5 Jan
NZ$242
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Save an average of 15% on thousands of hotels when you're signed in
Jiminy Peak Mountain Resort
37 Corey Rd Hancock MA
The price is NZ$423 per night from 4 Jan to 5 Jan
NZ$423
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ...
Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$199 per night from 4 Jan to 5 Jan
NZ$199
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
Monument Mountain Motel
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
Shaker Mill Inn
2 Oak Street West Stockbridge MA
The price is NZ$216 per night from 21 Dec to 22 Dec
NZ$216
21 Dec - 22 Dec
includes taxes & fees
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$261 per night from 4 Jan to 5 Jan
NZ$261
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 20 Dec to 21 Dec
NZ$182
20 Dec - 21 Dec
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all propertiesLowest 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.
Western Massachusetts hotels essential information
Accommodation | 1,478 hotels |
|---|---|
Lowest Price | NZ$182 |
Highest Price | NZ$423 |
Popular hotels | Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham, Berkshire Valley Inn, Jiminy Peak Mountain Resort, Hampton Inn & Suites Berkshires-Lenox, Monument Mountain Motel, Shaker Mill Inn, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG |
Most recent Western Massachusetts hotel reviews
lastminute.co.nz Verified Review
5 / 5
A magical, magical New England weekend at The Red Lion Inn. The room was so warm, the bed and pillows were so comfortable and just the right firmness. The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night. Check in was a breeze, staff were warm and welcoming.
Highly recommend making reservations at their Tavern or Dining Area.
Several small cafes and charming local shops close by for Christmas shopping
A verified traveller stayed at The Red Lion Inn
Posted 3 days ago
More ways to explore Western Massachusetts
Top picks
Hotels
- Waltham Accommodation
- Chelsea Accommodation
- Woburn Accommodation
- Hotels in Accord
- Peabody Accommodation
- Revere Accommodation
- Everett Accommodation
- Pet Friendly Hotels in North Shore
- Quincy Accommodation
- Wellesley Accommodation
- The Berkshires Accommodation
- Cambridge Accommodation
- Swampscott Accommodation
- Kauai Accommodation
- Rockland Accommodation
- Martha's Vineyard Accommodation
- Pet Friendly Hotels in Cambridge
- Salem Accommodation
- Hotels in North End
- Framingham Accommodation
- Maui Accommodation
- Oahu Accommodation
- Luxury Hotels in Somerville
- Hotels in Back Bay
- Norwood Accommodation
- Beach Hotels in Heartland
- Brookline Accommodation
Flights