Western Massachusetts Winery Accommodation

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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 AU$557 per night from 23 Dec to 24 Dec
AU$557
23 Dec - 24 Dec
includes taxes & fees
Located in Great Barrington, The Old Inn On The Green is a 5-minute drive from Dry Hill and 7 minutes from Questing.
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 AU$196 per night from 5 Jan to 6 Jan
AU$196
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at Shaker Mill Inn in West Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ebenezer II Gifts and Antiques.
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 AU$129 per night from 4 Jan to 5 Jan
AU$129
4 Jan - 5 Jan 2026
includes taxes & fees
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
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 AU$86 per night from 1 Jan to 2 Jan
AU$86
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Pleasant Valley Motel West Stockbridge in West Stockbridge, you'll be near the beach, within a 15-minute drive of Tanglewood Music Center and ...
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
With a stay at Chesapeake Inn of Lenox in Lenox, you'll be next to a golf course, just a 5-minute walk from Tanglewood Music Center and a 2-minute drive from ...
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
With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River ...
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 AU$228 per night from 7 Jan to 8 Jan
AU$228
7 Jan - 8 Jan 2026
includes taxes & fees
A stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires places you in the heart of Great Barrington, within a 5-minute drive of Housatonic ...
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 AU$128 per night from 4 Jan to 5 Jan
AU$128
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes ...
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
With a stay at Lantern House Motel in Great Barrington, you'll be in the mountains, a 4-minute walk from Housatonic River and a 2-minute drive from Housatonic ...
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
AU$86
Highest Price
AU$557
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

Most recent Western Massachusetts hotel reviews