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

7 Jan - 8 Jan
Tonight
Check prices in Western Massachusetts for tonight, 7 Jan - 8 Jan
8 Jan - 9 Jan
Tomorrow night
Check prices in Western Massachusetts for tomorrow night, 8 Jan - 9 Jan

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
Fully refundableReserve now, pay when you stay
The price is NZ$383 per night from 20 Jan to 21 Jan
NZ$383
includes taxes & fees
20 Jan - 21 Jan
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
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
Fully refundableReserve now, pay when you stay
The price is NZ$205 per night from 14 Jan to 15 Jan
NZ$205
includes taxes & fees
14 Jan - 15 Jan
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 ...
The Yankee, Trademark Collection by Wyndham
Berkshire Valley Inn

Berkshire Valley Inn

2.5 out of 5
2541 Hancock Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is NZ$242 per night from 8 Jan to 9 Jan
NZ$242
includes taxes & fees
8 Jan - 9 Jan
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. ...
Berkshire 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$369 per night from 8 Jan to 9 Jan
NZ$369
includes taxes & fees
8 Jan - 9 Jan
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 our reviews. Popular ...
Jiminy 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$252 per night from 14 Jan to 15 Jan
NZ$252
includes taxes & fees
14 Jan - 15 Jan
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 helpful staff ...
Hampton 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
The price is NZ$132 per night from 20 Jan to 21 Jan
NZ$132
includes taxes & fees
20 Jan - 21 Jan
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Monument Mountain Motel
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is NZ$204 per night from 8 Jan to 9 Jan
NZ$204
includes taxes & fees
8 Jan - 9 Jan
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 ...
Shaker 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$319 per night from 15 Jan to 16 Jan
NZ$319
includes taxes & fees
15 Jan - 16 Jan
Book a stay at this spa hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is NZ$197 per night from 23 Jan to 24 Jan
NZ$197
includes taxes & fees
23 Jan - 24 Jan
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
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
1,383 hotels
Lowest Price
NZ$132
Highest Price
NZ$383
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, an IHG Hotel

Most recent Western Massachusetts hotel reviews

Life House Berkshires
What a makeover!
5 / 5
Beautifully curated. You can barely believe it's a former roadside motel.
A verified traveller stayed at Life House Berkshires
Posted 1 day ago
Life House Berkshires

More ways to explore Western Massachusetts