Find Winery Hotels in The Berkshires, MA

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Check availability on The Berkshires Winery Hotels

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

Top 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 ₩397,825
₩480,051 total
includes taxes & fees
Jul 28 - Jul 29
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 ₩266,131
₩291,946 total
includes taxes & fees
Jul 28 - Jul 29
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 ₩173,740
₩194,068 total
includes taxes & fees
Jul 27 - Jul 28
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, (986)
"Clean and convenient. Great value."
The price is ₩95,368
₩104,619 total
includes taxes & fees
Jul 29 - Jul 30
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."
The price is ₩129,019
₩144,109 total
includes taxes & fees
Jul 27 - Jul 28
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 ₩207,143
₩231,378 total
includes taxes & fees
Aug 14 - Aug 15
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 ₩138,759
₩154,994 total
includes taxes & fees
Aug 7 - Aug 8
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."
Andrea 1-night trip
Posted 7 days ago
Best Western Plus Berkshire Hills Inn & Suites
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
" The friendliness and excellent service received from the staff. While we stayed at the Yankee, we expected a delivery from UPS and the staff at the registration ensured that we would be informed as soon as it arrived at the Yankee. There was a delay from UPS and it caused us some stress. The Yankee staff made sure we were kept informed of the delivery. Their concern was greatly appreciated. Thank you."
Gerrie 4-night trip
Posted 8 days ago
The Yankee, Trademark Collection by Wyndham