Holiday Homes in Pittsfield State Forest
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Our top choices for Pittsfield State Forest holiday homes
Holiday Home in Sherwood Forest
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is €329
includes taxes & fees
8 Jan - 9 Jan 2026
Holiday Home in Great Barrington
Home in Great Barrington9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
Cameron M.
The price is €224
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Florida
Florida Mountain Log Cabin10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is €319
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Lebanon Springs
Historic Berkshires Home Near Tanglewood, Trails & Wineries8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
Wendy D.
The price is €361
includes taxes & fees
28 Jan - 29 Jan 2026
Holiday Home in Great Barrington
Family Ski Getaway in the Berkshires9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
Kathy C.
The price is €260
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Pittsfield
3-bedroom house in beautiful Berkshires, close to amenities!The price is €288
includes taxes & fees
10 Jan - 11 Jan 2026
Holiday Home in West Sand Lake
Treat yourself at the stunning June Farms Wellness Huts!10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
SteveS
The price is €477
includes taxes & fees
28 Jan - 29 Jan 2026
Holiday Home in Lee
Sun Filled Lenox Retreat - Minutes to Tanglewood!9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
Sarah D.
The price is €400
includes taxes & fees
4 Jan - 5 Jan 2026
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 State Forest Hotel Reviews
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
Find out more about Pittsfield State Forest
Pittsfield State Forest Holiday Homes information
Number of reviews | 129 |
|---|---|
Accommodation | 363 Holiday Homes |
Lowest Price | €224 |
Highest Price | €1,195 |
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