Home Vacation Home Rentals By Owner In Stockbridge, MA

Showing 20 Of 38 Vacation Rentals
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Exceptional(7)

$842.34

/ Nightly
Private Vacation Home

Light Filled Modern Rustic 3-bedroom house in charming Stockbridge

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(29)

$584.19

/ Nightly
Private Vacation Home

Secluded Family Home in Serene Stockbridge Woods

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(68)

$603.18

/ Nightly
Private Vacation Home

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

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(18)

$610.93

/ Nightly
Private Vacation Home

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

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(10)

$612.4

/ Nightly
Private Vacation Home

Waterfront log cabin down a private dirt road next to Tanglewood

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(16)

$643.39

/ Nightly
Private Vacation Home

Autumn in Stockbridge

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(99)

$670.2

/ Nightly
Private Vacation Home

Modern Cottage in the heart of the Berkshires with new exterior flex space!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(148)

$682.38

/ Nightly
Private Vacation Home

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

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$754.43

/ Nightly
Private Vacation Home

Chic Homestead Experience, Pick-and-Eat Gardens!

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 7

Sleeps
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$795.6

/ Nightly
Private Vacation Home

Elegant & private light-filled privacy

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps
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$577.81

/ Nightly
Private Vacation Home

Meadow`s Edge: A Modern Retreat

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(40)

$855.62

/ Nightly
Private Vacation Home

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(14)

$856.18

/ Nightly
Private Vacation Home

Historic Rectory Retreat in Stockbridge – Getaway for 8-12 Guests

Stockbridge, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 12

Sleeps
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Exceptional(24)

$912.59

/ Nightly
Private Vacation Home

Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(17)

$1367.58

/ Nightly
Private Vacation Home

Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10

Stockbridge, Massachusetts, United States

Bed 5

Bed

Bath 5

Bath

Sleep 10

Sleeps
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Exceptional(109)

$1403.32

/ Nightly
Private Vacation Home

A Grand property in Historic Stockbridge

Stockbridge, Massachusetts, United States

Bed 6

Bed

Bath 7

Bath

Sleep 12

Sleeps
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Exceptional(37)

$408.45

/ Nightly
Private Vacation Home

A Charming Mid 1800's Stockbridge Farmhouse.

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(61)

$999.34

/ Nightly
Private Vacation Home

InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba

Stockbridge, Massachusetts, United States

Bed 12

Bed

Bath 7

Bath

Sleep 24

Sleeps
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$1369.44

/ Nightly
Private Vacation Home

Comfortable & Casual Stockbridge Retreat with View & Pool

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
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Exceptional(26)

$420.27

/ Nightly
Private Vacation Home

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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View 38 Private vacation home

Home Most popular vacation rentals in Stockbridge

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Exceptional(26)

$408.45

/ Nightly
Private vacation home

A Charming Mid 1800's Stockbridge Farmhouse.

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$451.38

/ Nightly
Private vacation home

Two Blocks from the Red Lion Inn & next to Berkshire Theater

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$442.33

/ Nightly
Cabin

Lakeshore cabin with beach and dock

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(26)

$441.78

/ Nightly
Cottage

Light-filled Carpenter's Cottage

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(26)

$415.15

/ Nightly
Private vacation home

Stockbridge Home: Walk to Town Beach!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(26)

$410.31

/ Nightly
Private vacation home

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(26)

$409.20

/ Nightly
Private vacation home

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(26)

$344.63

/ Nightly
Private vacation home

Stockbridge pied-à-terre

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps
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Exceptional(26)

$310.50

/ Nightly
Private vacation home

Hearth House | Prime Location!

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 5

Sleeps
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Exceptional(26)

$320.47

/ Nightly
Cottage

Cozy Winter Retreat

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Most Popular Cities in Massachusetts