Holiday Homes in Beartown State Forest

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Our top choices for Beartown State Forest holiday homes

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 €329
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is €343
includes taxes & fees
5 Jan - 6 Jan 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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 €240
includes taxes & fees
21 Jan - 22 Jan 2026
Home in Great Barrington

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is €302
includes taxes & fees
12 Jan - 13 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!

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 €339
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is €282
includes taxes & fees
5 Jan - 6 Jan 2026
Family Ski Getaway in the Berkshires

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
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."
United States
Sarah D.
The price is €417
includes taxes & fees
22 Jan - 23 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €440
includes taxes & fees
5 Jan - 6 Jan 2026
Cheerful 3-bedroom cottage with woodstove

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 €465
includes taxes & fees
27 Dec - 28 Dec
Near Tanglewood: Historic Summer Retreat

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 €432
includes taxes & fees
3 Jan - 4 Jan 2026
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 €485
includes taxes & fees
4 Jan - 5 Jan 2026
Great Barrington Get Away

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 €1,032
includes taxes & fees
19 Jan - 20 Jan 2026
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

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 €1,163
includes taxes & fees
25 Dec - 26 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is €440
includes taxes & fees
4 Jan - 5 Jan 2026
Artists’ Hideaway in Old Chatham

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 €515
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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 €1,553
includes taxes & fees
18 Jan - 19 Jan 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

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 €800
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 5-bedroom house in charming Lee with WiFi

Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now!
Egremont
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
The price is €1,234
includes taxes & fees
19 Jan - 20 Jan 2026
Catamount, Zip Line, Private Setting, Book Now!
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 Beartown State Forest Hotel Reviews

Find out more about Beartown State Forest

Beartown State Forest Holiday Homes information

Number of reviews
169
Accommodation
402 Holiday Homes
Lowest Price
€240
Highest Price
€1,553

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