Find Winery Hotels in Lenox, MA

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Pick from 15 Lenox Winery Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Chesapeake Inn of Lenox
3.0 star property
7.2 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
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
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1000)
"What a pleasure it was to stay at the Cornell Inn! Unfortunately we were only there for one night, but one can definitely get a sense of how a property is even in a shorter timeframe. Now, the real gem at this property is the staff! From our check-in experience with Lorie to our F&B server, Lindsey whi went waaaaay out of her way to help us with an issue we had, and to Paige, front desk assistant manager who tied everything together and made our experience even that much better. I wish I...
The price is AED 448
AED 526 total
includes taxes & fees
17 Nov - 18 Nov
The Cornell Inn, Lenox
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (470)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is AED 509
AED 638 total
includes taxes & fees
14 Nov - 15 Nov
Whistler's Inn Bed & Breakfast
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1000)
" Thank you to our very kind and welcoming hosts. We had a beautiful room, very clean, with a view of the water. It was an excellent stay."
The price is AED 356
AED 398 total
includes taxes & fees
19 Nov - 20 Nov
The Yankee, Trademark Collection by Wyndham
Gateways Inn & Restaurant
3.0 star property
7.8 out of 10, Good, (185)
"very comfortable and pleasant hotel."
The price is AED 719
AED 839 total
includes taxes & fees
14 Nov - 15 Nov
Gateways Inn & Restaurant
Kemble Inn
3.5 star property
8.8 out of 10, Excellent, (31)
"wonderfully restored old mansion. Rooms were charming... nicely designed. In fact the entire facility has been thoughtfully brought into today's design standards. Very accomodating staff... although many appeared to be a training mode. Need to improve the professionalism a bit. They have a new general manager (had only been there about 2 weeks when we visited)... seems he has a number of things on his agenda that will improve the property even more. Food was good... but not wonderful. ...
Kemble Inn
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
Hampton Inn & Suites Berkshires-Lenox
2.5 star property
9.2 out of 10, Wonderful, (1000)
"Staff was extremely friendly. The last morning we were there this sweet woman in the breakfast area told us that the kitchen was going to be closing and asked if I wanted anything else. It was about five of 10. I said eggs and she went into the kitchen and brought me out eggs, ketchup, salt, and pepper and a dish right to my table so super sweet, my husband and I will definitely be coming back "
The price is AED 434
AED 485 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn & Suites Berkshires-Lenox
Howard Johnson by Wyndham Lenox
2.0 star property
7.6 out of 10, Good, (700)
"It served our needs"
The price is AED 290
AED 324 total
includes taxes & fees
14 Nov - 15 Nov
Howard Johnson by Wyndham Lenox
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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