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25 Jul - 27 Jul
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Featured Cottages in Pittsfield State Forest

Charlemont Retreat on Chickley River w/ EV Charger
Enjoy the serene surroundings and well-maintained deck adjacent to this house.

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
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cozy cabin with a fireplace, dining area, and forest views.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cozy Becket Cottage Escape w/ Lake Access!
Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Interior

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
Expansive Upstate Home w/ Home Theater!
Enjoy a spacious open-plan living area with a kitchen and comfortable seating, perfect for relaxing and taking in the views.

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Spacious Historic Home in the Berkshires!
Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Relax in a serene garden setting surrounded by mature trees and lush greenery, with a stone fire pit and Adirondack chairs.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Luxury Vacation Rental in the Berkshires!
Enjoy cooking in this well-equipped kitchen with a range hood, double oven, and granite countertop.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Private Hot Tub: Hudson Valley Cabin Retreat!
Enjoy meals at the large dining table with a bench, surrounded by a stone fireplace and rustic decor.

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Stockbridge Home: Walk to Town Beach!
Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Berkshire Hideaway w/ Fire Pit & Playground!
Relax on the spacious deck with a wooden railing, surrounded by a lush forest.

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Interior

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Picturesque Cottage With Sunroom on Ashmere Lake!
Enjoy the serene view from the deck, where you can sit and relax with a wicker chair and table.

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
12-acre Vacation Rental in the Berkshires!
Property grounds

12-acre Vacation Rental in the Berkshires!

3.0 star property
12-acre Vacation Rental in the Berkshires!
Massachusetts Vacation Rental w/ Deck & Grill
4 bedrooms, desk, laptop workspace, bed sheets

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
Woodland Zen by Avantstay Modern Design + Patio
Interior

Woodland Zen by Avantstay Modern Design + Patio

3.0 star property
Woodland Zen by Avantstay Modern Design + Patio
Elegant Pittsfield Home Near Downtown & Skiing!
Front of property

Elegant Pittsfield Home Near Downtown & Skiing!

3.0 star property
Elegant Pittsfield Home Near Downtown & Skiing!
Stockbridge Retreat w/ Pool & Hot Tub!
Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
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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