Photo by Photo courtesy of Berkshire Visitors Bureau

Find Winery Hotels in The Berkshires, MA

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Check availability on The Berkshires Winery Hotels

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Top The Berkshires Winery Hotels

Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
"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 SAR 380
SAR 424 total
includes taxes & fees
23 Dec - 24 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Loft, Private Bathroom (Skylight Loft) | Premium bedding, iron/ironing board, rollaway beds, free WiFi
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn
Exterior
Berkshire Valley 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 SAR 503
SAR 562 total
includes taxes & fees
18 Dec - 19 Dec
Berkshire Valley Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock 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 SAR 491
SAR 549 total
includes taxes & fees
4 Jan - 5 January 2026
East Rock Inn
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is SAR 547
SAR 1,416 total
includes taxes & fees
10 Dec - 11 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

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

Great Barrington
The price is SAR 1,163
SAR 1,471 total
includes taxes & fees
10 Dec - 11 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
The price is SAR 1,276
SAR 2,205 total
includes taxes & fees
10 Dec - 11 Dec
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

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 SAR 548
SAR 639 total
includes taxes & fees
6 Jan - 7 January 2026
Gateways Inn & Restaurant
Premium bedding, memory foam beds, individually decorated
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is SAR 446
SAR 517 total
includes taxes & fees
5 Jan - 6 January 2026
Nautical Nest
Room, 1 King Bed, Balcony, Garden View | Balcony view
Wm. Farmer & Sons

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 SAR 659
SAR 745 total
includes taxes & fees
11 Dec - 12 Dec
Wm. Farmer & Sons
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.
View all properties

Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room was spacious and clean, the jetted tub was a nice treat, and the breakfast was fresh. "
Christina 2-night trip
Posted 6 days ago
The Yankee, Trademark Collection by Wyndham

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