Winery Hotels & Resorts in The Berkshires from NZ$126

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Winery Hotels

Tonight
24 Jul - 25 Jul
Tomorrow
25 Jul - 26 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Best The Berkshires Winery Hotels

The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is NZ$579
includes taxes & fees
7 Aug - 8 Aug
The Old Inn On The Green
Shaker Mill Inn
Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (416)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is NZ$309
includes taxes & fees
30 July - 31 July
Shaker Mill Inn
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1012)
"Very nice stay"
The price is NZ$234
includes taxes & fees
31 July - 1 Aug
Best Western Plus Berkshire Hills Inn & Suites
Pleasant Valley Motel West Stockbridge
Orchids bloom in a serene, well-maintained setting.

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (985)
"Clean and convenient. Great value."
The price is NZ$126
includes taxes & fees
29 July - 30 July
Pleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox
Sit and enjoy conversation or dining in this serene outdoor space surrounded by lush greenery.

Chesapeake Inn of Lenox

3.0 star property
7.4 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
Monument Mountain Motel
Comfortable retreat with a neatly made bed, wall-mounted lamps, and a convenient nightstand.

Monument Mountain Motel

2.5 star property
9.0 out of 10, Wonderful, (731)
"Helpful, friendly staff. Clean, convenient, quiet."
Monument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Relax in a welcoming space with comfortable seating and a stunning chandelier.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (717)
"Nice outdoor seating areas, big pool, clean nicely appointed toom"
The price is NZ$279
includes taxes & fees
14 Aug - 15 Aug
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Enjoy a spacious room with a modern kitchen, dining area, and comfortable seating space.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1008)
"Good basic convenient accommodation in a heavily touristy area."
The price is NZ$187
includes taxes & fees
6 Aug - 7 Aug
Quality Inn
Lantern House Motel
Surrounded by a white picket fence, this serene gazebo features a central lantern and comfortable seating for relaxation.

Lantern House Motel

2.5 star property
8.2 out of 10, Very good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel
Garden Gables Inn
Stunning mountain retreat with a spacious porch and multiple windows, surrounded by snow-covered trees and a well-lit pathway.

Garden Gables Inn

4.0 star property
9.2 out of 10, Wonderful, (57)
"Rosie the Innkeeper was very friendly and welcoming. The breakfast was outstanding and so was our waitress. Can’t wait to go back again. "
Garden Gables Inn
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

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Clean, smells good, newer amenities. Totally improved since two years ago. "
Olga 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Lenox