Photo by Photo courtesy of Berkshire Visitors Bureau

Winery Hotels & Resorts in The Berkshires from NZ$212

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Winery Hotels

This weekend
Next weekend

Our top choices for The Berkshires hotels with winery

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, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is NZ$212
includes taxes & fees
27 Jan - 28 Jan
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

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 NZ$241
includes taxes & fees
20 Jan - 21 Jan
Berkshire Valley Inn

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37)
"The room was clean and comfortable wi will back next year:) "
United States
Nadya
The price is NZ$238
includes taxes & fees
20 Jan - 21 Jan
East Rock Inn

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 NZ$650
includes taxes & fees
8 Jan - 9 Jan
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is NZ$995
includes taxes & fees
8 Jan - 9 Jan
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Gateways Inn & Restaurant

Gateways Inn & Restaurant
3.0 star property
Lenox
8.0 out of 10, Very good, (195)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is NZ$303
includes taxes & fees
8 Jan - 9 Jan
Gateways Inn & Restaurant

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (128)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is NZ$238
includes taxes & fees
8 Jan - 9 Jan
Nautical Nest

Wm. Farmer & Sons

Wm. Farmer & Sons
2.5 star property
Hudson
9.2 out of 10, Wonderful, (77)
"We had a lovely stay. They upgraded our room & we had the most cozy & charming suite. Would absolutely stsy here again. "
United States
Natalie
The price is NZ$320
includes taxes & fees
11 Jan - 12 Jan
Wm. Farmer & Sons

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109)
"Great experience, looking forward to staying again."
United States
Greg
The price is NZ$290
includes taxes & fees
14 Jan - 15 Jan
Changing Times Boutique Country Lodging
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.

Top The Berkshires Hotel Reviews

Explore a world of travel with Expedia