Search Vacation Homes in Pittsfield State Forest

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Pittsfield State Forest holiday homes

Interior

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 HK$1,143
HK$2,940 total
includes taxes & fees
8 Apr - 9 Apr
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,440
HK$2,665 total
includes taxes & fees
13 Apr - 14 Apr
Florida Mountain Log Cabin
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is HK$1,587
HK$2,464 total
includes taxes & fees
20 Apr - 21 Apr
Home in Great Barrington
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$959
HK$2,742 total
includes taxes & fees
12 Apr - 13 Apr
Near Tanglewood: Historic Summer Retreat
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (13 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,587
HK$2,482 total
includes taxes & fees
10 Apr - 11 Apr
Cozy Riverside Berkshires Retreat
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 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 HK$1,587
HK$3,506 total
includes taxes & fees
13 Apr - 14 Apr
North Getaway Cottage
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!
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 HK$2,109
HK$3,870 total
includes taxes & fees
9 Apr - 10 Apr
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Interior

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 HK$1,185
HK$3,031 total
includes taxes & fees
8 Apr - 9 Apr
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Dining

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 HK$910
HK$1,590 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Home in Pownal VT
Terrace/patio

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 HK$2,159
HK$3,745 total
includes taxes & fees
21 Apr - 22 Apr
Treat yourself at the stunning June Farms Wellness Huts!
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is HK$1,852
HK$3,182 total
includes taxes & fees
12 Apr - 13 Apr
The Greylock Cabin
TV, fireplace

Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham
Old Chatham
The price is HK$1,265
HK$3,971 total
includes taxes & fees
13 Apr - 14 Apr
Artists’ Hideaway in Old Chatham
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (35 reviews)
"A very special, well equipped, and comfortable house with a great kitchen, bedrooms and bathrooms as well as a lovely enclosed porch and outdoor area in an amazing location. Wonderful home with all amenities and thoughtful details provided for guests. A short walk to charming town and across from a beautiful hiking area. Excellent stay!"
United States
Susan
The price is HK$2,814
HK$5,691 total
includes taxes & fees
8 Apr - 9 Apr
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Private kitchen

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 HK$821
HK$2,605 total
includes taxes & fees
10 Apr - 11 Apr
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
9.0 out of 10, Wonderful, (7 reviews)
"Kind and responsive host."
United States
Javier
The price is HK$1,262
HK$4,243 total
includes taxes & fees
11 Apr - 12 Apr
Comfortable Berkshires retreat on mtn resort, SISO
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
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"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$4,437
HK$10,410 total
includes taxes & fees
9 Apr - 10 Apr
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (6 reviews)
"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.
The price is HK$1,215
HK$2,302 total
includes taxes & fees
12 Apr - 13 Apr
Sweet Cozy Victorian in Housatonic. Close to everything.
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 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 HK$2,069
HK$4,366 total
includes taxes & fees
22 Apr - 23 Apr
Treetop Hideaway in Tyringham
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,372
HK$4,355 total
includes taxes & fees
17 Apr - 18 Apr
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.0 out of 10, Wonderful, (2 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is HK$1,372
HK$2,423 total
includes taxes & fees
12 Apr - 13 Apr
Renovated house. Built in 1890s. No neighbors in sight.
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 Pittsfield State Forest Hotel Reviews

Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"Heard dogs barking. No big deal. Would bring my pets here. "
Heather 3-night trip
Posted 3 hours ago
Comfort Inn & Suites East Greenbush - Albany

Find out more about Pittsfield State Forest

Pittsfield State Forest Vacation Homes information

Number of reviews
195
Accommodation
363 Vacation Homes
Lowest Price
HK$1,590
Highest Price
HK$10,410