Find Winery Hotels in The Berkshires, MA
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Top The Berkshires Winery Hotels
Our top choices for The Berkshires hotels with winery

The Old Inn On The Green
The Old Inn On The Green
9.2 out of 10, Wonderful, (88)
The price is NT$8,866
NT$10,698 total
includes taxes & fees
Sep 1 - Sep 2

Shaker Mill Inn
Shaker Mill Inn
9.6 out of 10, Exceptional, (422)
The price is NT$4,891
NT$5,366 total
includes taxes & fees
Sep 4 - Sep 5

Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
8.6 out of 10, Excellent, (1004)
The price is NT$3,248
NT$3,628 total
includes taxes & fees
Sep 2 - Sep 3

Pleasant Valley Motel West Stockbridge
Pleasant Valley Motel West Stockbridge
6.8 out of 10, (998)
The price is NT$2,125
NT$2,331 total
includes taxes & fees
Sep 4 - Sep 5

Chesapeake Inn of Lenox
Chesapeake Inn of Lenox
7.4 out of 10, Good, (8)

Monument Mountain Motel
Monument Mountain Motel
8.8 out of 10, Excellent, (744)

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
9.4 out of 10, Exceptional, (732)
The price is NT$4,616
NT$5,156 total
includes taxes & fees
Sep 7 - Sep 8

Quality Inn
Quality Inn
8.2 out of 10, Very Good, (1006)
The price is NT$2,832
NT$3,164 total
includes taxes & fees
Sep 14 - Sep 15
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
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Hotels near popular The Berkshires Attractions
- Hotels near Tanglewood Music Center
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Williams College
- Hotels near National Shrine of the Divine Mercy
- Hotels near Massachusetts Museum of Contemporary Art
- Hotels near Mount Greylock
- Hotels near The Clark Art Institute
- Hotels near Norman Rockwell Museum
- Hotels near Ski Butternut
- Hotels near Lee Premium Outlets
The Berkshires Hotels by Star Rating
Explore more hotels
- FairBridge Inn Express
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Howard Johnson by Wyndham Lenox
- The Porches Inn at Mass MoCA
- Hampton Inn & Suites Berkshires-Lenox
- Best Western Plus Berkshire Hills Inn & Suites
- The Constance by the Lenox Collection
- Howard Johnson by Wyndham Williamstown
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Hotel On North
- Courtyard by Marriott Lenox Berkshires
- Fairfield Inn & Suites by Marriott Williamstown
- The Whitlock
- Williamstown Motel
- Monument Mountain Motel
- Cozy Corner Motel
- The Cornell Inn, Lenox & The Berkshires
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