Find Winery Hotels in Lenox, MA
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Top Lenox Winery Hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
9.0 out of 10, Wonderful, (1003)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
Elisabeth
The price is SAR 380
SAR 424 total
includes taxes & fees
16 Dec - 17 Dec
Gateways Inn & Restaurant
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
Josephine
The price is SAR 548
SAR 639 total
includes taxes & fees
6 Jan - 7 January 2026
Brook Farm Inn
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
Christopher
East Rock Inn
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
Laura
The price is SAR 491
SAR 549 total
includes taxes & fees
4 Jan - 5 January 2026
Berkshire Valley Inn
Williamstown
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
Scott
The price is SAR 503
SAR 562 total
includes taxes & fees
8 Dec - 9 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is SAR 547
SAR 1,412 total
includes taxes & fees
8 Dec - 9 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
Kaye S.
The price is SAR 507
SAR 1,396 total
includes taxes & fees
8 Dec - 9 Dec
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
The price is SAR 1,163
SAR 1,471 total
includes taxes & fees
8 Dec - 9 Dec
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 Lenox Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
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Hotels near popular Lenox Attractions
- Hotels near Tanglewood Music Center
- Hotels near The Mount
- Hotels near Lenox Library
- Hotels near Shakespeare and Company
- Hotels near Wyndhurst Golf & Club
- Hotels near Ventfort Hall Mansion and Gilded Age Museum
- Hotels near Kennedy Park
- Hotels near Lenox Mountain
- Hotels near Wood's Pond
- Hotels near Pleasant Valley Wilderness Sanctuary
Lenox Hotels by Star Rating
Explore more hotels
- The Whitlock
- Wagon Wheel Inn
- The Dewey
- The Kemble- Built by a US Secretary of State in Lenox
- Gateways Inn & Restaurant
- Whistler's Inn Bed & Breakfast
- Vacation Village in the Berkshires
- Hotel Downstreet, an Ascend Collection Hotel
- Berkshire Mountain Lodge
- The Williams Inn
- Holiday Inn & Suites Pittsfield-Berkshires by IHG
- The Red Lion Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- The Black Swan Lee - Lenox, an Ascend Collection Hotel
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Best Western Plus Berkshire Hills Inn & Suites
- Hotel On North
- Huttopia Berkshires
- Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
- Quality Inn