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Our top choices for Pittsfield State Forest holiday homes

Florida Mountain Log Cabin

Florida Mountain Log Cabin
2.0 star property
Florida
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

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Monterey
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is HK$6,597
HK$13,793 total
includes taxes & fees
18 Jan - 19 Jan 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
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$4,425
HK$10,365 total
includes taxes & fees
19 Dec - 20 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
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!

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Hillsdale
10.0 out of 10, Exceptional, (1)
"Beautiful house! It was a big house and we loved all the rooms and how they were decorated! When we first arrived the heat wasn’t working and the host had someone there with the half hour fixing the problem. Beautiful quite area as well "
United States
Gabrielle T.
The price is HK$4,271
HK$10,203 total
includes taxes & fees
27 Dec - 28 Dec
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

The Lakeshore House

The Lakeshore House
Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is HK$3,773
HK$6,239 total
includes taxes & fees
19 Dec - 20 Dec
The Lakeshore House

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
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

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."
United States
Sharon K.
The price is HK$1,134
HK$2,909 total
includes taxes & fees
22 Dec - 23 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,634
HK$2,650 total
includes taxes & fees
12 Jan - 13 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!

Home in Great Barrington

Home in Great Barrington
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

The Greylock Cabin

The Greylock Cabin
Florida
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

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
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

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
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$2,645
HK$4,554 total
includes taxes & fees
21 Dec - 22 Dec
Cozy. Clean. Free bagel shop. 3 Fireplaces.

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
Pittsfield
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!

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (23)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$2,241
HK$4,409 total
includes taxes & fees
27 Dec - 28 Dec
Near Tanglewood: Historic Summer Retreat

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
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$4,077
HK$7,117 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 5-bedroom house in charming Lee with WiFi

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
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

Great Barrington Get Away

Great Barrington Get Away
Great Barrington
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

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
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

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Valatie
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$4,165 total
includes taxes & fees
21 Dec - 22 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
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
16,846
Accommodation
363 Vacation Homes
Lowest Price
HK$600
Highest Price
HK$1,713