Search Vacation Homes in Beartown State Forest

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Beartown State Forest vacation homes

Interior
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

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.
$335 nightly
The price is $374
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

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.
$351 nightly
The price is $392
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$230 nightly
The price is $257
Jan 5 - Jan 6, 2026
Total with taxes and fees
Home in Great Barrington
Exterior detail
3-bedroom house in beautiful Berkshires, close to amenities!

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

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
$285 nightly
The price is $318
Jan 12 - Jan 13, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
Interior
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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.
$329 nightly
The price is $368
Jan 8 - Jan 9, 2026
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Interior
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Jan 4 - Jan 5, 2026
Total with taxes and fees
Family Ski Getaway in the Berkshires
Smart TV, books
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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.
$412 nightly
The price is $460
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Property grounds
Cheerful 3-bedroom cottage with woodstove

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.
$450 nightly
The price is $503
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior
Near Tanglewood: Historic Summer Retreat

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.
$474 nightly
The price is $531
Dec 27 - Dec 28
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
Outdoor dining
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!

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.
$442 nightly
The price is $494
Jan 3 - Jan 4, 2026
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Smart TV, DVD player, books, stereo
Great Barrington Get Away

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.
$496 nightly
The price is $554
Jan 4 - Jan 5, 2026
Total with taxes and fees
Great Barrington Get Away
Terrace/patio
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

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.
$1,055 nightly
The price is $1,182
Jan 19 - Jan 20, 2026
Total with taxes and fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
TV, fireplace, printers
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness 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
$1,189 nightly
The price is $1,328
Dec 25 - Dec 26
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
TV, fireplace
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
$448 nightly
The price is $502
Jan 4 - Jan 5, 2026
Total with taxes and fees
Artists’ Hideaway in Old Chatham
3 bedrooms, iron/ironing board, WiFi, bed sheets
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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.
$526 nightly
The price is $588
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Property grounds
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

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.
$1,587 nightly
The price is $1,773
Jan 18 - Jan 19, 2026
Total with taxes and fees
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Fridge, microwave, oven, stovetop
Spacious 5-bedroom house in charming Lee with WiFi

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.
$819 nightly
The price is $915
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
TV, fireplace
Catamount, Zip Line, Private Setting, Book Now!

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.
$1,233 nightly
The price is $1,410
Jan 19 - Jan 20, 2026
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Beartown State Forest Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 11 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Beartown State Forest

Beartown State Forest Vacation Homes information

Number of reviews
169
Accommodation
402 Vacation Homes
Lowest Price
$257
Highest Price
$1,773