Search Vacation Homes in Pittsfield State Forest

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Our top choices for Pittsfield State Forest holiday homes

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,260
HK$3,068 total
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is HK$1,214
HK$2,051 total
includes taxes & fees
6 Jan - 7 Jan 2026
Home in Great Barrington

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,430
HK$2,637 total
includes taxes & fees
22 Dec - 23 Dec
Florida Mountain Log Cabin
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is HK$1,167
HK$3,024 total
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries
8.4 out of 10, Very good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
Perfect House In Hillsdale, Brings Friends & Fam

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
The price is HK$1,575
HK$2,316 total
includes taxes & fees
21 Dec - 22 Dec
Family Ski Getaway in the Berkshires
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
Sweet Cozy Victorian in Housatonic. Close to everything.
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."
United States
SteveS
The price is HK$2,143
HK$4,364 total
includes taxes & fees
15 Jan - 16 Jan 2026
Treat yourself at the stunning June Farms Wellness Huts!
The price is HK$1,712
HK$2,746 total
includes taxes & fees
15 Jan - 16 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!

Holiday Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is HK$2,169
HK$3,552 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Greylock Cabin

Holiday Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is HK$2,334
HK$4,163 total
includes taxes & fees
19 Dec - 20 Dec
Great Barrington Get Away
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is HK$2,094
HK$3,764 total
includes taxes & fees
20 Dec - 21 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is HK$3,392
HK$5,953 total
includes taxes & fees
23 Dec - 24 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Holiday Home in Old Chatham

Artists’ Hideaway in Old Chatham
The price is HK$1,484
HK$3,653 total
includes taxes & fees
19 Dec - 20 Dec
Artists’ Hideaway in Old Chatham
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is HK$2,505
HK$5,699 total
includes taxes & fees
19 Dec - 20 Dec
Comfortable Berkshires retreat on mtn resort, SISO
10.0 out of 10, Exceptional, (60)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is HK$2,101
HK$4,174 total
includes taxes & fees
22 Dec - 23 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,404
HK$10,333 total
includes taxes & fees
20 Dec - 21 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Holiday Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,112
HK$5,162 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is HK$4,660
HK$8,157 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hancock Village Inn Near Jiminy Peak
8.0 out of 10, Very good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,151
HK$5,796 total
includes taxes & fees
24 Dec - 25 Dec
Spacious 5-bedroom house in charming Lee with WiFi
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.
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Top Pittsfield State Forest Hotel Reviews

Find out more about Pittsfield State Forest

Pittsfield State Forest Vacation Homes information

Number of reviews
248
Accommodation
363 Vacation Homes
Lowest Price
HK$2,051
Highest Price
HK$10,333