Find Winery Hotels in The Berkshires, MA

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Check availability on The Berkshires Winery Hotels

Tonight
30 Jan - 31 Jan
Tomorrow
31 Jan - 1 Feb
This weekend
31 Jan - 2 Feb
Next weekend
7 Feb - 9 Feb

Compare The Berkshires Winery Hotels room rates, reviews, and availability. Most hotels are fully refundable.

The Old Inn On The Green
Room

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (81)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
The price is AED 973
AED 1,175 total
includes taxes & fees
2 Feb - 3 Feb
The Old Inn On The Green
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (407)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
3 Feb - 4 Feb
Shaker Mill Inn
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Great place for an overnight with my friend!"
The price is AED 356
AED 398 total
includes taxes & fees
5 Feb - 6 Feb
Best Western Plus Berkshire Hills Inn & Suites
Pleasant Valley Motel West Stockbridge
Exterior

Pleasant Valley Motel West Stockbridge

2.0 star property
6.8 out of 10, (960)
"The room and bathroom were very clean. "
The price is AED 221
AED 243 total
includes taxes & fees
31 Jan - 1 Feb
Pleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox
Exterior

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
Room

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (698)
"Rooms have been recently renovated and were clean and spotless. Great comfortable room with convenient gas station and sandwich shop across the street as well as several other eateries close by. Owner and staff were very friendly and made me feel welcome. I will definitely come back here in the future...... Good job 👍"
The price is AED 244
AED 273 total
includes taxes & fees
2 Feb - 3 Feb
Monument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.2 out of 10, Wonderful, (681)
"My kids said this was their favorite hotel ever likely thanks to the cool game room. It’s pretty annoying they don’t accept animals and don’t have any food options in the hotel. The breakfast was nice "
The price is AED 558
AED 624 total
includes taxes & fees
23 Feb - 24 Feb
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
Exterior

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1005)
"All went well"
The price is AED 311
AED 347 total
includes taxes & fees
5 Feb - 6 Feb
Quality Inn
Lantern House Motel
Room

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
Front of property

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.
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