Stockbridge Vacation Rentals

Compare 6 vacation rentals.
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Make Stockbridge your next getaway

Stockbridge, MA vacation rentals

Top Stockbridge property types

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House rentals

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Apartments

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Cottages

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Popular amenities for Stockbridge vacation rentals

Popular
Dog-friendly Hot tub Internet
Steps to Downtown Stockbridge: Home w/ Patio!
2 Bedroom | 2 Bath | Sleeps 5

Steps to Downtown Stockbridge: Home w/ Patio! - Stockbridge, MA

$148 avg / night
(excludes fees and taxes)
2 Mi to Norman Rockwell Museum: Stockbridge Apt!
1 Bedroom | 1 Bath | Sleeps 2

2 Mi to Norman Rockwell Museum: Stockbridge Apt! - Stockbridge, MA

$122 avg / night
(excludes fees and taxes)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
2 Bedroom | 2 Bath | Sleeps 4

Cozy Stockbridge Cabin - Walk to Beach & Lake! - Stockbridge, MA

$253 avg / night
(excludes fees and taxes)
4.5 (2)
Tranquil 3 BR Stockbridge House w/ Private Deck!
3 Bedroom | 1.5 Bath | Sleeps 6

Tranquil 3 BR Stockbridge House w/ Private Deck! - Stockbridge, MA

$356 avg / night
(excludes fees and taxes)
4.95 (19)
Stockbridge Retreat w/ Pool & Hot Tub!
4 Bedroom | 3.5 Bath | Sleeps 10

Stockbridge Retreat w/ Pool & Hot Tub! - Stockbridge, MA

$1,606 avg / night
(excludes fees and taxes)
5.0 (3)

View 1 more homes

Browse more vacation rental amenities in Stockbridge

Pool | Lake view | Ocean view | Water view | Waterfront | A/C | Washer/dryer | Balcony | Bikes | Ping-pong table

Recent Stockbridge guest reviews

We come every January for my husband’s birthday to just sit by the fire & read. It’s the perfect quiet and comfortable get away!
Becky . | Jan 2026
Wonderful property and Great location. Looking forward to renting next year.
Nancy . | Aug 2025
This cozy cabin is a bit rustic, but clean & welcoming.
Sarah . | Jul 2025
Stockbridge vacation rental FAQ

Yes. 32 of our Stockbridge vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Stockbridge vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Stockbridge team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Stockbridge, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

Appalachian Mountains   |   New England   |   West Stockbridge   |   Lee   |   Lenox   |   Richmond   |   Great Barrington   |   Monterey   |   Pittsfield   |   New Marlborough   |   Sheffield   |   Becket   |   Hillsdale   |   Otis   |   Hinsdale   |   Dalton   |   Sandisfield   |   Lanesborough   |   Copake   |   Hancock   |   Hollowville   |   Windsor   |   Tolland   |   Huntington   |   Hudson   |   East Schodack   |   Cummington   |   Coxsackie   |   Athens   |   Averill Park   |   Hannacroix   |   Pine Plains   |   Catskill   |   West Sand Lake   |   Williamstown   |   Massachusetts
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