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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Featured Cottages in Stockbridge

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!
Private Hot Tub: Hudson Valley Cabin Retreat!
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!
Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Outdoor dining

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

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

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Skiing & Hiking: Water-view Home in the Berkshires
Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
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!
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Interior

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!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Lakefront Otis Home w/ Stunning Views & Boats!
Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Stockbridge Home: Walk to Town Beach!
Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Waterfalls and Trails at 'the Mills At Green Hole'
Front of property

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
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!
Stockbridge Retreat w/ Pool & Hot Tub!
Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Front of property

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

3.0 star property
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
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 Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Liked the fact there are 2 pools, an indoor and an outdoor."
MARK 2-night trip
Posted 15 hours ago
Vacation Village in the Berkshires

Frequently asked questions

How much do cottages in Stockbridge cost?
Prepare to pay between and per night for cottages in Stockbridge. Whatever your budget, a terrific stay is only a few clicks away on Expedia. 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 Stockbridge?
Take advantage of your vacation days and choose from 67 cottages in Stockbridge. Yearning for a place where you can immerse yourself in nature? Expedia will help you find the ideal escape in a few easy clicks.
Why book your cottage in Stockbridge with Expedia?
Reserving a cottage in Stockbridge is as simple as working out your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to affordable stays and cottages that come with conveniences like a kitchen, Expedia has something for all traveler tastes. As for epic deals? We've have them as well!