Stockbridge Vacation Rentals - HolidayHomes base64Hash Stockbridge Vacation Rentals - HolidayHomes

Stockbridge Vacation Rentals

Browse 161 available vacation homes and compared across 9 trusted partners

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Top-Rated Vacation rentals in Stockbridge

Book the highest-rated Stockbridge vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Stockbridge
Location! Location! Berkshire Glamour (and comfort) Meets Town And Country
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House Stockbridge
Vacation home with BBQ, garden & patio | City view
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House Stockbridge
Fully equipped spacious house with BBQ & terrace | Pets allowed
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Cabin Stockbridge
Cottage with terrace & BBQ
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House Stockbridge
Modern Cottage in the heart of the Berkshires with new exterior flex space!
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House Stockbridge
Fully equipped vacation home with yard, terrace & grill
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House Stockbridge
House with barbeque, terrace & garden
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House Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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House Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse.
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Cabin Stockbridge
Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!
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Apartment Stockbridge
Clean & Modern space with a mix of original warmth and charming renovation.
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House Stockbridge
House with yard, patio & barbecue | Nature view
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House Stockbridge
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
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House Stockbridge
House with barbecue
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House Stockbridge
House with yard, BBQ & terrace
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Top 15 most Recommended Vacation Rentals in Stockbridge

Discover your ideal Stockbridge vacation rental with real-time comparisons of 161 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Stockbridge
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with patio, garden & grill

Stockbridge, Berkshire County, Massachusetts, United States
This cozy cabin in Stockbridge accommodates 8 guests and features a welcoming fireplace for a warm and inviting atmosphere.
from $376
per night
(33)
View deal
Cabin Stockbridge
Cabin ∙ 8 guests ∙ 4 bedrooms

Cottage with barbeque & terrace

Stockbridge, Berkshire County, Massachusetts, United States
This cozy cabin in Stockbridge accommodates 8 guests and features a welcoming fireplace for a warm and inviting atmosphere.
-11%
$485
from $432
per night
(6)
View deal
House Stockbridge
House ∙ 10 guests ∙ 3 bedrooms

Vacation home with yard & BBQ

Stockbridge, Berkshire County, Massachusetts, United States
Spacious house rental in Stockbridge for 10 guests featuring a cozy fireplace and ample parking for your convenience.
from $224
per night
(20)
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House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly pleasant vacation home with terrace, barbeque & garden | Good for workation | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
Charming house rental in Stockbridge accommodating 6 guests with a cozy fireplace and a spacious yard for outdoor activities.
from $339
per night
(52)
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House Stockbridge
House ∙ 8 guests ∙ 4 bedrooms

House with barbecue, patio & yard | Nature view

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge accommodates 8 guests and features a cozy fireplace for a warm and inviting stay.
from $646
per night
(12)
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Condo Stockbridge
Condo ∙ 6 guests ∙ 3 bedrooms

Fully equipped spacious condo with pool & patio

Stockbridge, Berkshire County, Massachusetts, United States
This cozy condo in Stockbridge accommodates 6 guests and features a welcoming fireplace perfect for relaxation.
from $220
per night
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House Stockbridge
House ∙ 7 guests ∙ 4 bedrooms

Child-friendly charming vacation home with barbeque, yard & patio | Nature view | Perfect for remote work

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $272
per night
(81)
View deal
House Stockbridge
House ∙ 3 guests ∙ 1 bedroom

House with 1 room for 3 persons

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge accommodates 3 guests and features convenient parking for your stay.
from $296
per night
(24)
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Cabin Stockbridge
Cabin ∙ 7 guests ∙ 3 bedrooms

Fully equipped spacious cabin with grill

Stockbridge, Berkshire County, Massachusetts, United States
Cozy cabin in Stockbridge with a capacity for 7 guests and a fully equipped kitchen for your convenience.
from $396
per night
(8)
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