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Winery Hotels & Resorts in The Berkshires from AU$170

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Check availability on The Berkshires Winery Hotels

Best 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 AU$170
includes taxes & fees
21 Dec - 22 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Loft, Private Bathroom (Skylight Loft)
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 AU$203
includes taxes & fees
10 Dec - 11 Dec
Berkshire Valley Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen
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 AU$223
includes taxes & fees
5 Jan - 6 Jan 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 AU$575
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 AU$596
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 AU$895
includes taxes & fees
10 Dec - 11 Dec
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Room (King Room)
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 AU$265
includes taxes & fees
7 Jan - 8 Jan 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 AU$208
includes taxes & fees
5 Jan - 6 Jan 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 AU$299
includes taxes & fees
17 Dec - 18 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.
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Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Staff were awesome. Will stay again."
Kim 2-night trip
Posted 8 days ago
The Yankee, Trademark Collection by Wyndham

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