Search Winery Hotels in The Berkshires

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Winery Hotels

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

Our top choices for The Berkshires hotels with winery

Lake

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, (1,000 reviews)
"Beautiful place- beautiful views "
United States
Yanis
The price is £95
includes taxes & fees
18 May - 19 May
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
United States
Laura
The price is £107
includes taxes & fees
15 May - 16 May
East Rock Inn
Exterior

Berkshire Valley Inn

Berkshire Valley Inn
2.5 star property
Williamstown
9.2 out of 10, Wonderful, (567 reviews)
"Cozy, homey feel of our suite. You can tell the owner takes pride of her inn— cute Pinterest inspiration decoration in the room and lobby. The free breakfast and coffee is a great start to the morning. Close to Jiminy Peak, so easy to ski and come back before the kids fall asleep. "
United States
Sue
The price is £103
includes taxes & fees
13 May - 14 May
Berkshire Valley Inn
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is £157
includes taxes & fees
2 Jun - 3 Jun
Brook Farm Inn
Classic Queen - Room 8 | Premium bedding, down duvets, pillow-top beds, individually decorated

Garden Gables

Garden Gables
4.0 star property
Lenox
The price is £264
includes taxes & fees
18 May - 19 May
Garden Gables
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £277
includes taxes & fees
7 May - 8 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 £386
includes taxes & fees
3 May - 4 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Premium bedding, memory-foam beds, individually decorated

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (134 reviews)
"It was very quiet and well maintained. Attractive decor . Would stay again"
United States
Judith
The price is £122
includes taxes & fees
5 May - 6 May
Nautical Nest
Room, 1 King Bed, Balcony, Garden View | Egyptian cotton sheets, premium bedding, pillow-top beds, minibar

Wm. Farmer & Sons

Wm. Farmer & Sons
2.5 star property
Hudson
9.2 out of 10, Wonderful, (91 reviews)
"My stay was just lovely! Exactly what I was looking for. Everything smelled great, was beautiful to look it and the staff was sweet and accommodating! I’ll be back."
United States
Stephane
The price is £165
includes taxes & fees
4 May - 5 May
Wm. Farmer & Sons
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 reviews)
"The place is so authentic and beautiful, the owner is so kind and friendly, and we had really good experience "
United States
Tamir
The price is £161
includes taxes & fees
3 May - 4 May
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.
View all properties

Top The Berkshires Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The gentleman at the desk was extremely helpful and very friendly We enjoyed talking to him while having coffee"
Valerie 2-night trip
Posted 5 hours ago
Quality Inn Great Barrington

Explore a world of travel with Expedia