Find Winery Hotels in Pittsfield, MA
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Top Pittsfield Winery Hotels
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
9.0 out of 10, Wonderful, (1002)
"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 AED 403
AED 450 total
includes taxes & fees
4 Dec - 5 Dec
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 AED 539
AED 602 total
includes taxes & fees
30 Nov - 1 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
James F.
The price is AED 536
AED 1,386 total
includes taxes & fees
17 Nov - 18 Nov
Berkshire Valley Inn
Williamstown
9.2 out of 10, Wonderful, (564)
"The owners were very helpful and communicative, and the hotel room was clean, comfortable, and attractive, with all the amenities we needed. Thank you for a nice stay!"
Blithe
The price is AED 542
AED 606 total
includes taxes & fees
20 Nov - 21 Nov
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
Kaye S.
The price is AED 502
AED 1,373 total
includes taxes & fees
16 Nov - 17 Nov
Brook Farm Inn
Lenox
9.4 out of 10, Exceptional, (162)
"Beautiful inn - romantic and welcoming!"
Ronald
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Valatie
10.0 out of 10, Exceptional, (56)
"Great spot on the lake. Super quiet and relaxing."
vincent m.
The price is AED 992
AED 1,975 total
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
The price is AED 1,249
AED 2,105 total
includes taxes & fees
19 Nov - 20 Nov
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 Pittsfield Hotel Reviews
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
Quality Inn
10/10 Excellent
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Hotels near popular Pittsfield Attractions
- Hotels near Bousquet Ski Area
- Hotels near Hancock Shaker Village
- Hotels near Colonial Theater
- Hotels near Berkshire Museum
- Hotels near Barrington Stage Company
- Hotels near Guido's Marketplace
- Hotels near Berkshire Athenaeum
- Hotels near Canoe Meadows Wildlife Sanctuary
- Hotels near Crane Museum of Papermaking
- Hotels near Herman Melville's Arrowhead
Pittsfield Hotels by Star Rating
Explore more hotels
- Vacation Village in the Berkshires
- Hotel Downstreet, an Ascend Collection Hotel
- The Williams Inn
- Berkshires Untold
- The Red Lion Inn
- Quality Inn
- Comfort Inn & Suites East Greenbush - Albany
- The Black Swan Lee - Lenox, an Ascend Collection Hotel
- The Yankee, Trademark Collection by Wyndham
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Quality Inn
- Jiminy Peak Mountain Resort
- Huttopia Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- Monument Mountain Motel
- Courtyard by Marriott Lenox Berkshires
- Howard Johnson by Wyndham Lenox
- The Porches Inn at Mass MoCA
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires