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Our top choices for Pittsfield State Forest vacation homes

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is AED 397
AED 497 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,382 total
includes taxes & fees
16 Jun - 17 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AED 426
AED 749 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Home in Pownal VT

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 688
AED 1,527 total
includes taxes & fees
16 Jun - 17 Jun
stylish Berkshires Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is AED 876
AED 1,331 total
includes taxes & fees
17 Jun - 18 Jun
Home in Great Barrington

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 1,163 total
includes taxes & fees
17 Jun - 18 Jun
Cozy Riverside Berkshires Retreat

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is AED 868
AED 1,503 total
includes taxes & fees
17 Jun - 18 Jun
The Greylock Cabin

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 643
AED 2,045 total
includes taxes & fees
16 Jun - 17 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is AED 552
AED 1,416 total
includes taxes & fees
18 Jun - 19 Jun
Near Tanglewood: Historic Summer Retreat

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AED 1,098
AED 2,205 total
includes taxes & fees
17 Jun - 18 Jun
Treetop Hideaway in Tyringham

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 1,017
AED 1,825 total
includes taxes & fees
16 Jun - 17 Jun
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (25 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AED 744
AED 1,651 total
includes taxes & fees
16 Jun - 17 Jun
North Getaway Cottage

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 845
AED 1,390 total
includes taxes & fees
16 Jun - 17 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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 reviews)
"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 AED 1,068
AED 1,817 total
includes taxes & fees
16 Jun - 17 Jun
Treat yourself at the stunning June Farms Wellness Huts!

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AED 661
AED 1,567 total
includes taxes & fees
17 Jun - 18 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 1,154
AED 2,023 total
includes taxes & fees
17 Jun - 18 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is AED 876
AED 1,849 total
includes taxes & fees
7 Jul - 8 Jul
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is AED 1,374
AED 2,653 total
includes taxes & fees
12 Jul - 13 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
The price is AED 397
AED 497 total
includes taxes & fees
16 Jun - 17 Jun
Unique and Eclectic Small Town Suite Rental in Massachusetts

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 2,005 total
includes taxes & fees
16 Jun - 17 Jun
Comfortable Berkshires retreat on mtn resort, SISO
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