Find Winery Hotels in The Berkshires, MA

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Pick from 29 The Berkshires Winery Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (386)
"Wonderful place to stay in western Massachusetts."
The price is SAR 521
SAR 572 total
includes taxes & fees
6 Jum. II - 7 Jum. II
Shaker Mill Inn
The Barrington
View from room
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (99)
"As always, our stay at The Barrington was wonderful. The rooms are large, lovely and the bed comfortable. The service is great and everyone is so friendly and accommodating! The breakfast is delicious. We truly enjoy our stay, every time!"
The price is SAR 1,219
SAR 1,362 total
includes taxes & fees
6 Jum. II - 7 Jum. II
The Barrington
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Pool
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (651)
"I loved the staff and the accommodations. I’d recommend this property. "
The price is SAR 705
SAR 788 total
includes taxes & fees
9 Jum. II - 10 Jum. II
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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
Hampton Inn & Suites Berkshires-Lenox
Exterior
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1002)
"The bed was very uncomfortable "
The price is SAR 699
SAR 781 total
includes taxes & fees
25 Jum. II - 26 Jum. II
Hampton Inn & Suites Berkshires-Lenox
The Old Inn On The Green
Room
The Old Inn On The Green
4.0 star property
9.0 out of 10, Wonderful, (70)
"It was great experience. "
The price is SAR 1,088
SAR 1,265 total
includes taxes & fees
6 Jum. II - 7 Jum. II
The Old Inn On The Green
Monument Mountain Motel
Room
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (604)
"Very acceptable. No in-room coffee. "
The price is SAR 321
SAR 358 total
includes taxes & fees
6 Jum. II - 7 Jum. II
Monument Mountain Motel
The Yankee, Trademark Collection by Wyndham
Exterior
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1005)
"The staff was super friendly. The room was clean and I had no issues at all."
The price is SAR 478
SAR 534 total
includes taxes & fees
12 Jum. II - 13 Jum. II
The Yankee, Trademark Collection by Wyndham
Hampton Terrace Inn
Exterior
Hampton Terrace Inn
4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
Hampton Terrace Inn
The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1002)
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is SAR 439
SAR 510 total
includes taxes & fees
6 Jum. II - 7 Jum. II
The Cornell Inn, Lenox
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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.

Recent reviews of The Berkshires hotels
Expedia verified reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5/5 Excellent
Great place to stay
"The staff was super friendly. The room was clean and I had no issues at all."
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham