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, (78)
"Staying here was like stepping back in time. Lovely preservation of a historic inn. Food was wonderful. Stairs challenging, but worth the effort. We felt like John and Abigail Adams! "
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, (399)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is SAR 545
SAR 598 total
includes taxes & fees
14 Nov - 15 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, (1000)
"The staff was super nice & welcoming. "
The price is SAR 367
SAR 409 total
includes taxes & fees
8 Dec - 9 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 238
SAR 261 total
includes taxes & fees
5 Dec - 6 Dec
Pleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox
Exterior
Chesapeake Inn of Lenox
3.0 star property
7.2 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, (676)
"Monument Mountain is a great bargain for a no-frills roadside motel. "
The price is SAR 250
SAR 279 total
includes taxes & fees
14 Nov - 15 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, (671)
"Great hotel with nice staff and facilities. Close to grocery, restaurants and Stockbridge tourist attractions."
The price is SAR 571
SAR 638 total
includes taxes & fees
17 Nov - 18 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, (1000)
"Decent room at a decent price. Only put off by musty smell in room. "
The price is SAR 268
SAR 299 total
includes taxes & fees
27 Nov - 28 Nov
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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