Find Winery Hotels in Pittsfield, MA
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Our top choices for Pittsfield 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, (1000)
"Room was clean and the staff was super friendly and helpful!"
Ethan
$100 nightly
The price is $112
Jan 13 - Jan 14, 2026
Total with taxes and fees
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
$118 nightly
The price is $132
Jan 8 - Jan 9, 2026
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Wintery Cabin-Berkshires! Dog-friendly. 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.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2 out of 10, Wonderful, (564)
"We had a short but pleasant stay. "
Scott
$139 nightly
The price is $155
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
Christopher
$165 nightly
The price is $184
Dec 30 - Dec 31
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Historic Berkshires Home Near Tanglewood, Trails & WineriesLebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
Kaye S.
$332 nightly
The price is $372
Jan 8 - Jan 9, 2026
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer RetreatNew Lebanon
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
Paul S.
$428 nightly
The price is $479
Dec 27 - Dec 28
Total with taxes and fees
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/DryerGreat Barrington
$447 nightly
The price is $499
Dec 28 - Dec 29
Total with taxes and fees
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
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
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- Hotels near Berkshire Museum
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