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Find Winery Hotels in The Berkshires, MA

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Top The Berkshires Winery Hotels

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1005)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is AED 390
AED 436 total
includes taxes & fees
18 Dec - 19 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn

Berkshire Valley Inn

2.5 star property
Williamstown
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
United States
Scott
The price is AED 509
AED 569 total
includes taxes & fees
3 Dec - 4 Dec
Berkshire Valley Inn

East Rock Inn

2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
The price is AED 474
AED 529 total
includes taxes & fees
11 Dec - 12 Dec
East Rock Inn

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 535
AED 1,386 total
includes taxes & fees
10 Dec - 11 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington
The price is AED 1,080
AED 1,366 total
includes taxes & fees
30 Nov - 1 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is AED 730
AED 852 total
includes taxes & fees
30 Nov - 1 Dec
Gateways Inn & Restaurant

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (123)
"We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. "
United States
Robin
The price is AED 419
AED 486 total
includes taxes & fees
1 Dec - 2 Dec
Nautical Nest

Wm. Farmer & Sons

2.5 star property
Hudson
9.2 out of 10, Wonderful, (73)
"So beautifully preserved building. We had a beautiful room with sitting area overlooking the front of the hotel. Very easy to get to main streets and riverside. Restaurant was wonderful. "
United States
Vivienne
The price is AED 602
AED 680 total
includes taxes & fees
2 Dec - 3 Dec
Wm. Farmer & Sons

The Amelia

2.0 star property
Hudson
9.8 out of 10, Exceptional, (27)
"Nice place"
United States
Manuel
The price is AED 1,683
AED 1,902 total
includes taxes & fees
29 Nov - 30 Nov
The Amelia
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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Top The Berkshires Hotel Reviews

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