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25 Jul - 27 Jul
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Browse Select The Berkshires Cottages

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!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Skiing & Hiking: Water-view Home in the Berkshires
House (3 Bedrooms) | Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
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!
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!
House (2 Bedrooms) | Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Whitney by Avantstay Private Berkshires Estate
Stunning two-story house with a central entrance and beautifully manicured lawns.

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
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!
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!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cottage (1 Bedroom) | Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Stockbridge Home: Walk to Town Beach!
House (3 Bedrooms) | Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Enjoy cooking in this well-equipped kitchen with a large island, dishwasher, sink, and stove.

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
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!
Lakefront Otis Home w/ Stunning Views & Boats!
House (2 Bedrooms) | Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
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
House (3 Bedrooms) | 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!
House (5 Bedrooms) | 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!
House (4 Bedrooms) | Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Interior

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

3.0 star property
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Stylish room with a hardwood floor, wooden chair, and small table, featuring large windows and a staircase.

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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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Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between and per night. Whatever your budget, you'll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in The Berkshires?
Explore our 49 cottages in The Berkshires and then select your favourite. Whether you're organising a holiday with the whole fam or a break with pals, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in The Berkshires with Expedia?
Booking a cottage in The Berkshires is as easy as clicking on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for the best deals around? We've got them too!