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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Pittsfield State Forest and around

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Relax on a deck overlooking a serene body of water surrounded by lush greenery and trees.

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (83)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Charming historic cottage on scenic road to Mt. Greylock
Cozy home surrounded by lush vegetation.

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Lake Views & Dock Access - Pittsfield Cottage!
Traditional homes line the quiet street, each with a central chimney and green shutters.

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (4)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
Beachwood Cottage
Stroll through the serene garden, surrounded by lush trees and shrubs, and discover a tranquil atmosphere perfect for relaxation.

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Entire cottage in Berkshire Villiage
Situated in a wooded area, this charming house features a gabled roof and a welcoming front porch.

Entire cottage in Berkshire Villiage

3.0 star property
9.4 out of 10, Exceptional, (3)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Cozy cottage with pool, walking distance to lake
Relax on the front porch with a comfortable seating area.

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake
Grandparent’s Cottage 250 steps to the lake
Sun-loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Charlemont Retreat on Chickley River w/ EV Charger
Situated in a wooded area, this charming home offers a front porch with outdoor seating and a chimney.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Situated in a grassy area, this cozy home features a red-framed door and windows with string lights.

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (4)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Berkshires farm, 30+ guests, 50 acres
Situated on a grassy area, this charming home features a traditional two-story design with a prominent porch and a small attached structure.

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is €1,882
includes taxes & fees
1 Sept - 2 Sept
Berkshires farm, 30+ guests, 50 acres
Private Hot Tub: Hudson Valley Cabin Retreat!
House (3 Bedrooms) | Interior

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Luxury Vacation Rental in the Berkshires!
Relax in a serene outdoor setting with a central fire pit surrounded by Adirondack chairs.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Relax on the deck with a view of the surrounding forest, featuring a comfortable seating area with sofas and a chair.

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

10.0 out of 10, Exceptional, (3)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Guests can enjoy the cabin's expansive deck with seating and large windows offering a view of the surrounding forest.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Relax on the deck with comfortable seating and a decorative rug.

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (11)
"Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. "
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Expansive Upstate Home w/ Home Theater!
House (5 Bedrooms) | Interior

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Picturesque Cottage with Sunroom on Ashmere Lake!
Relax on the lakeside deck with a table and chairs, surrounded by a grassy area and offering unobstructed views of the lake.

Picturesque Cottage with Sunroom on Ashmere Lake!

9.6 out of 10, Exceptional, (24)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
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

FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"Will stay at again."
Michael 1-night trip
Posted 2 days ago
FairBridge Inn Express