Compare Ski Hotels in Western Massachusetts

Start date: Check-in selected.
To Date
End date: Check-out

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

22 Dec - 23 Dec
Tonight
Check prices in Western Massachusetts for tonight, 22 Dec - 23 Dec
23 Dec - 24 Dec
Tomorrow night
Check prices in Western Massachusetts for tomorrow night, 23 Dec - 24 Dec

Featured Western Massachusetts Ski Hotels

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is NZ$221 per night from 4 Jan to 5 Jan
NZ$221
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 ...
Opens in a new windowVacation 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
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 4 Jan to 5 Jan
NZ$147
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 pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd Williamstown MA
The price is NZ$243 per night from 4 Jan to 5 Jan
NZ$243
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. ...
Opens in a new windowBerkshire Valley Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3 out of 5
37 Corey Rd Hancock MA
The price is NZ$425 per night from 4 Jan to 5 Jan
NZ$425
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 ...
Opens in a new windowJiminy Peak Mountain Resort
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 4 Jan to 5 Jan
NZ$202
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 ...
Opens in a new windowHampton Inn & Suites Berkshires-Lenox
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
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 ...
Get rates
Opens in a new windowMonument Mountain Motel
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
The price is NZ$221 per night from 5 Jan to 6 Jan
NZ$221
5 Jan - 6 Jan 2026
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 ...
Opens in a new windowShaker Mill Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 6 Jan to 7 Jan
NZ$262
6 Jan - 7 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 ...
Opens in a new windowFairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
The price is NZ$180 per night from 25 Dec to 26 Dec
NZ$180
25 Dec - 26 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 ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Don't see what you're looking for?
See all available properties in Western Massachusetts
View all properties
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.

Western Massachusetts hotels essential information

Accommodation
1,478 hotels
Lowest Price
NZ$147
Highest Price
NZ$425
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

MGM Springfield
lastminute.co.nz Verified Review
5 / 5
The check-in was smooth and easy. The room was clean and well decorated. The room is was not basic beige, it was stylish. The beds and pillows were very comfortable.
A verified traveller from Tiverton stayed at MGM Springfield
Posted 2 days ago
MGM Springfield

More ways to explore Western Massachusetts