Compare Winery Hotels in Western Massachusetts

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Featured Western Massachusetts Winery Hotels

The Old Inn On The Green

The Old Inn On The Green

4 out of 5
134 Hartsville-New Marlborough Rd Great Barrington MA
The price is NZ$639 per night from 23 Dec to 24 Dec
NZ$639
23 Dec - 24 Dec
includes taxes & fees
Stay at this inn in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Questing and New Marlborough Town Library are located ...
Opens in a new windowThe Old Inn On The Green
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
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
Fully refundable
The price is NZ$148 per night from 4 Jan to 5 Jan
NZ$148
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
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Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is NZ$99 per night from 1 Jan to 2 Jan
NZ$99
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this motel in West Stockbridge. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the clean rooms in their reviews. Popular attractions ...
Opens in a new windowPleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

3 out of 5
210 West Street Lenox MA
Stay at this golf B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris House ...
Opens in a new windowChesapeake Inn of 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 ...
Opens in a new windowMonument Mountain Motel
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
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 5 Jan to 6 Jan
NZ$147
5 Jan - 6 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 breakfast and the helpful ...
Opens in a new windowQuality Inn Great Barrington
Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Opens in a new windowLantern House Motel
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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.

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Western Massachusetts hotels essential information

Accommodation
1,478 hotels
Lowest Price
NZ$99
Highest Price
NZ$639
Popular hotels
The Old Inn On The Green, Shaker Mill Inn, Best Western Plus Berkshire Hills Inn & Suites, Pleasant Valley Motel West Stockbridge, Chesapeake Inn of Lenox, Monument Mountain Motel, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Quality Inn Great Barrington, Lantern House Motel

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