Find Winery Hotels in Western Massachusetts, MA

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Pick from 29 Western Massachusetts Winery Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Old Inn On The Green
Room

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (79)
"There is a high-end restaurant at the Inn that has wonderful food. Delicious breakfasts (and Sunday Brunch) down the road at The Southfield Store were included. You can take a lovely back road walk past a beaver pond that starts from the parking lot. Employees were friendly and helpful. Multiple other protected area hikes in the neighborhood. We felt we lucked out picking this place."
The price is SAR 995
SAR 1,157 total
includes taxes & fees
24 Nov - 25 Nov
The Old Inn On The Green
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (400)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is SAR 544
SAR 597 total
includes taxes & fees
24 Nov - 25 Nov
Shaker Mill Inn
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.4 out of 10, Very Good, (1010)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is SAR 339
SAR 378 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (956)
"Well located near attractions "
The price is SAR 221
SAR 243 total
includes taxes & fees
27 Nov - 28 Nov
Pleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox
Exterior

Chesapeake Inn of Lenox

3.0 star property
7.4 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
Monument Mountain Motel
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (678)
"Nice people operating a very clean, comfortable motel. A bargain."
The price is SAR 250
SAR 279 total
includes taxes & fees
24 Nov - 25 Nov
Monument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (672)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is SAR 571
SAR 637 total
includes taxes & fees
25 Nov - 26 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1054)
"The young man who worked the Saturday evening shift until 11 ,was a true gentleman "
The price is SAR 267
SAR 299 total
includes taxes & fees
8 Dec - 9 Dec
Quality Inn
Lantern House Motel
Room

Lantern House Motel

2.5 star property
8.2 out of 10, Very Good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel
Garden Gables Inn
Front of property

Garden Gables Inn

4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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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