Stockbridge Vacation Rentals - HolidayHomes base64Hash Stockbridge Vacation Rentals - HolidayHomes

Stockbridge Vacation Rentals

Browse 182 available vacation homes and compared across 7 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

We use AI to generate the short summary in each offer below, check full description before booking.
House Stockbridge

Vacation home with BBQ, garden & patio | City view

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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

Stockbridge Village Cottage With Mountain View’s and walk to town

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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

House with barbecue, patio & yard | Nature view

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Cabin Stockbridge

Cottage with 4 bedrooms for 8 persons

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Cabin Stockbridge

Cottage with terrace & BBQ

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House Stockbridge

Location! Location! Berkshire Glamour (and comfort) Meets Town And Country

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House Stockbridge

Family-friendly wonderful house with garden, patio & private pool

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House Stockbridge

Child-friendly vacation home with garden, terrace & grill | Mountain view | Good for workation | Pets allowed

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House Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse.

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House Stockbridge

Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay

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House Stockbridge

House with garden, barbeque & terrace | Lake view

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Cabin Stockbridge

Cabin with yard, grill & patio | Mountain view

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Top 15 most Recommended Vacation Rentals in Stockbridge

Discover your ideal Stockbridge vacation rental with real-time comparisons of 182 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
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 $349
per night
(44)
View deal
House Stockbridge
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped spacious house with BBQ & terrace | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge accommodates 6 guests and features a cozy fireplace for a warm atmosphere.
from $319
per night
(177)
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House Stockbridge
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly ample house with barbecue, terrace & garden | Nature view | Good for workation | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
Charming house rental in Stockbridge for 8 guests featuring a cozy fireplace and a spacious yard for outdoor activities.
from $502
per night
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Condo Stockbridge
Condo ∙ 7 guests ∙ 3 bedrooms

Children-friendly condo with jacuzzi | Mountain view | Perfect for remote work | Pets allowed

Stockbridge, Berkshire County, Massachusetts, United States
This spacious condo in Stockbridge accommodates 7 guests and features a cozy fireplace for added comfort.
from $83
per night
(9)
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Cabin Stockbridge
Cabin ∙ 6 guests ∙ 2 bedrooms

Cottage with patio | Lake view

Stockbridge, Berkshire County, Massachusetts, United States
This cozy cabin in Stockbridge accommodates 6 guests and features beautiful lakeview amenities for a tranquil getaway.
from $173
per night
(39)
View deal
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 $317
per night
(82)
View deal
House Stockbridge
House ∙ 6 guests ∙ 2 bedrooms

Vacation home with garden, hot tub & grill | Lake view

Stockbridge, Berkshire County, Massachusetts, United States
This house rental in Stockbridge accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $198
per night
(32)
View deal
Cabin Stockbridge
Cabin ∙ 2 guests ∙ 1 bedroom

Cottage with 1 bedroom for 2 persons

Stockbridge, Berkshire County, Massachusetts, United States
Cozy cabin in Stockbridge accommodates 2 guests and features a charming fireplace for a warm, inviting atmosphere.
from $311
per night
(18)
View deal
Apartment Stockbridge
Apartment ∙ 2 guests ∙ 1 bedroom

Holiday apartment with patio | Pets are welcome

Stockbridge, Berkshire County, Massachusetts, United States
Cozy apartment rental in Stockbridge for 2 with a fully equipped kitchen and pets allowed.
from $138
per night
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