Photo by Photo courtesy of Berkshire Visitors Bureau
Find Winery Hotels in The Berkshires, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Winery Hotels
Our top choices for The Berkshires hotels with winery
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1,005 reviews)
"Clean room, nice staff , decent breakfast. Overall a good stay . "
Anindita
The price is NT$3,072
NT$3,432 total
includes taxes & fees
Mar 24 - Mar 25
9.6 out of 10, Exceptional, (38 reviews)
"The room was clean and comfortable wi will back next year:) "
Nadya
The price is NT$3,966
NT$4,430 total
includes taxes & fees
Mar 20 - Mar 21
9.2 out of 10, Wonderful, (567 reviews)
"We had a short but pleasant stay. "
Scott
The price is NT$3,847
NT$4,297 total
includes taxes & fees
Feb 25 - Feb 26
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
Christopher
8.0 out of 10, Very Good, (197 reviews)
"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"
Miguel
The price is NT$5,948
NT$6,942 total
includes taxes & fees
Feb 25 - Feb 26
9.6 out of 10, Exceptional, (129 reviews)
"Very cute, great location in town, nice and quiet"
Michael
The price is NT$3,758
NT$4,359 total
includes taxes & fees
Mar 5 - Mar 6
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
Greg
The price is NT$4,714
NT$5,280 total
includes taxes & fees
Feb 25 - Feb 26
9.2 out of 10, Wonderful, (80 reviews)
"We had a lovely stay. They upgraded our room & we had the most cozy & charming suite. Would absolutely stsy here again. "
Natalie
The price is NT$5,305
NT$5,995 total
includes taxes & fees
Feb 25 - Feb 26
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
Quality Inn
10/10 Excellent
Explore a world of travel with Expedia
- Hotels near Goose Pond Reservation
- Romantic Hotels in Lenox
- Four Seasons Hotels in Monterey
- Hotel Wedding Venues Hotels in Stockbridge
- Lee Hotels
- Hotels with smoking rooms in Westfield
- Hotels near Ski Butternut
- Hotels with a Pool in Great Barrington
- Hotels near Mahaiwe Performing Arts Center
- Rv Parks in Otis
- B&B in Stockbridge
- 4 Star Hotels in Great Barrington
- Hotels with a Pool in Stockbridge
- Country Houses in Beartown State Forest
- Resorts & Hotels with Spas in Sheffield
- Casino Hotels in Great Barrington
- Hotels with smoking rooms in Great Barrington
- Resorts & Hotels with Spas in Great Barrington
- Inns in Beartown State Forest
- Hotels near Chesterwood
- B&B in Great Barrington
- 5 Star Hotels in Becket
- Great Barrington Hotels
- Hotels with an Indoor Pool in The Berkshires
- Golf Hotels in Pittsfield
- Cheap Hotels in The Berkshires
- South Lee Hotels
- Historic Hotels in Lenox
- Hotels near National Shrine of the Divine Mercy
- Hotels with Bars in Pittsfield
- Stockbridge Hotels
- Hotels with smoking rooms in Lee
- Pet-Friendly Hotels in Lee
- Family Hotels in Sheffield
- Pet-Friendly Hotels in Pittsfield
- Resorts in Otis
- Historic Hotels in Richmond
- Blandford Hotels
- Boutique Hotels in The Berkshires
- Family Hotels in Monterey
- Hotels near Tyringham Cobble
- Hotel Wedding Venues Hotels in Great Barrington
- Pet-Friendly Hotels in The Berkshires
- Hotels with Hot Tubs in Lee
- Otis Hotels
- Hotels with a Pool in Sheffield
- Ski Hotels in Stockbridge
- Cheap Hotels in Pittsfield
- Hotels with an Indoor Pool in Pittsfield
- Hotels with an Indoor Pool in Lenox
- Family Hotels in The Berkshires
- Flights to South Lee
- Flights from Dallas (DFW) to Great Barrington (GBR)
- Flights to Stockbridge
- Flights from Chicago (ORD) to Great Barrington (GBR)
- Flights to Alford
- Flights to Southfield
- Flights from Granville
- Flights from South Egremont
- Flights from Walter J. Koladza
- Flights to The Berkshires
- Flights from Chester
- Flights from Lee
- Flights from Phoenix (PHX) to Great Barrington (GBR)
- Flights from Denver (DEN) to Great Barrington (GBR)
- Flights to Sheffield
- Pyramid Lake
- Visit Housatonic
- Visit Sandisfield
- National Shrine of the Divine Mercy
- Visit The Berkshires
- Norman Rockwell Museum
- Maple Corner Farm Cross Country Ski Area
- Otis Ridge
- Visit Great Barrington
- Visit Monterey
- Visit Lee
- Greenock Country Club
- Kushi Institute
- Animagic Museum of Animation
- Mission House
- Sandisfield Vacations
- Visit South Lee
- Lee Premium Outlets
- Becket Land Trust Historic Quarry
- Berkshire Botanical Garden
- South Lee Vacations
- Hertz Rental Cars in Mill River
- Guerin Rental Cars in Monterey
- Keddy By Europcar Rental Cars in Monterey
- Fox Rental Cars Rental Cars in New Marlborough
- Car rental Sheffield
- Ok Mobility Rental Cars in Otis
- Car rental South Egremont
- Thrifty Car Rental Rental Cars in Otis
- Addcar rental Rental Cars in Lee
- Car rental Lee
- Car rentals near Otis Ridge