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Our top choices for Pittsfield hotels with a golf course
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (989)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
Dwight
The price is NT$2,867
NT$3,203 total
includes taxes & fees
Dec 19 - Dec 20
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (707)
"Great hospitality "
regina maria
The price is NT$3,370
NT$3,764 total
includes taxes & fees
Jan 4 - 2026/1/5
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1001)
"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 NT$3,146
NT$3,514 total
includes taxes & fees
Jan 15 - 2026/1/16
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington BerkshiresGreat Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
Tom
The price is NT$2,352
NT$2,628 total
includes taxes & fees
Dec 28 - Dec 29
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
MARIA J
The price is NT$2,697
NT$3,013 total
includes taxes & fees
Dec 18 - Dec 19
9.0 out of 10, Wonderful, (789)
"This place is so peaceful and the staff is always helpful "
Leona
The price is NT$3,108
NT$4,175 total
includes taxes & fees
Jan 11 - 2026/1/12
5.4 out of 10, (810)
"Room spotless and staff helpful."
William
The price is NT$2,512
NT$2,806 total
includes taxes & fees
Jan 17 - 2026/1/18
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
Edward
The price is NT$3,275
NT$3,659 total
includes taxes & fees
Jan 4 - 2026/1/5
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 Red Lion Inn
10/10 Excellent
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- Frelinghuysen Morris House and Studio
- Pleasant Valley Wilderness Sanctuary
- Visit Housatonic
- Kushi Institute
- Visit Hancock
- Crane Museum of Papermaking
- Berkshire Botanical Garden
- National Shrine of the Divine Mercy
- Lee Premium Outlets
- South Lee Vacations
- Canoe Meadows Wildlife Sanctuary
- Mount Greylock State Reservation Visitor Center
- Visit South Lee
- Norman Rockwell Museum
- Charles H. Baldwin & Sons
- Animagic Museum of Animation
- Visit Lenox
- Greenock Country Club
- Visit Middlefield
- Bousquet Ski Area
- Mission House
- Visit Lanesborough
- Visit Dalton
- Visit Lee
- Visit West Stockbridge
- Lenox Mountain