Search Vacation Homes in Pittsfield State Forest

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Pittsfield State Forest

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is ¥22,041
¥32,826 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is ¥23,951
¥58,430 total
includes taxes & fees
Sep 24 - Sep 25
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is ¥27,331
¥74,934 total
includes taxes & fees
Aug 26 - Aug 27
Perfect House In Hillsdale, Brings Friends & Fam

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is ¥43,935
¥78,619 total
includes taxes & fees
Sep 11 - Sep 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is ¥27,639
¥44,496 total
includes taxes & fees
Sep 2 - Sep 3
Home in Great Barrington

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ¥23,657
¥71,217 total
includes taxes & fees
Aug 26 - Aug 27
Comfortable Berkshires retreat on mtn resort, SISO

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is ¥29,976
¥70,543 total
includes taxes & fees
Aug 27 - Aug 28
NEW RENO Historic Creamery in Berkshires w/hot tub

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is ¥55,103
¥75,995 total
includes taxes & fees
Aug 26 - Aug 27
Bungalow in the Berkshires

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

The price is ¥28,095
¥47,138 total
includes taxes & fees
Aug 26 - Aug 27
3-bedroom house in beautiful Berkshires, close to amenities!

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is ¥29,755
¥66,062 total
includes taxes & fees
Sep 4 - Sep 5
North Getaway Cottage

Experience Timeless Elegance in The Edith Wharton Room!

The price is ¥30,475
¥44,709 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Edith Wharton Room!

Treat yourself at the stunning June Farms Wellness Huts!

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."
The price is ¥38,880
¥68,438 total
includes taxes & fees
Aug 31 - Sep 1
Treat yourself at the stunning June Farms Wellness Huts!

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is ¥31,592
¥69,614 total
includes taxes & fees
Aug 26 - Aug 27
Near Tanglewood: Historic Summer Retreat

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is ¥33,502
¥75,008 total
includes taxes & fees
Sep 1 - Sep 2
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is ¥80,523
¥153,740 total
includes taxes & fees
Aug 26 - Aug 27
Hancock Village Inn at Jiminy Peak

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (17)
"This was a freshly renovated historic home - very spacious, well equipped kitchen, comfy living room & beds and a beautiful deck (wish the weather cooperated...). The large grounds provided lots of privacy. Easy to get to from NY, CT and VT. Limited cell service in the area - which was a plus for escaping, yet easy access to the property's wifi. Short drives to Lenox were very scenic."
The price is ¥32,929
¥71,274 total
includes taxes & fees
Sep 5 - Sep 6
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is ¥43,494
¥87,317 total
includes taxes & fees
Aug 31 - Sep 1
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is ¥47,756
¥83,708 total
includes taxes & fees
Sep 8 - Sep 9
Great Barrington Get Away

Spacious 5-bedroom house in charming Lee with WiFi

The price is ¥62,450
¥117,191 total
includes taxes & fees
Sep 2 - Sep 3
Spacious 5-bedroom house in charming Lee with WiFi

Upstate Lakefront-king bed, fire pit, fireplace,kayak, pontoon boat cruise

10.0 out of 10, Exceptional, (1)
"This sturdy, small house has everything you need to enjoy a get-away by a pretty lake. Lakeview always available through the large living-room windows and convenient & spacious dining area. 2 porches with seating are lit in evenings for a cozy feel. In addition, there is a large side/back yard with a fire pit, seating & ambiance lights. Other than not being handicap accessible, (steps to get in & steep steps with railings to the upstairs bedrooms), it is a really cute house! Host left fruit &...
The price is ¥27,639
¥52,044 total
includes taxes & fees
Sep 8 - Sep 9
Upstate Lakefront-king bed, fire pit, fireplace,kayak, pontoon boat cruise
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield State Forest Hotel Reviews

Find out more about Pittsfield State Forest

Find out more about Pittsfield State Forest

Pittsfield State Forest Vacation Homes information

Number of reviews
Accommodation
399 Vacation Homes
Lowest Price
¥23,657
Highest Price
¥23,657

Explore a world of travel with Expedia

Explore a world of travel with Expedia