Home Vacation Home Rentals By Owner In Stockbridge, MA

Showing 38 Of 38 Vacation Rentals
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Exceptional(25)

$317.15

/ Nightly
Private Vacation Home

Stockbridge Village in Summer

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps
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Exceptional(15)

$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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$367.22

/ Nightly
Private Vacation Home

Cozy, welcoming Berkshires cottage – perfect home base & place to unplug!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(4)

$392.39

/ Nightly
Private Vacation Home

Brand New Barn House w/ EV charger

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 4

Bath

Sleep 6

Sleeps
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Exceptional(2)

$402.45

/ Nightly
Private Vacation Home

Stockbridge Landings | 3 Mins To Tanglewood

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$404.36

/ Nightly
Private Vacation Home

3-bedroom duplex in Stockbridge on the river

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
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Exceptional(99)

$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(73)

$413.29

/ 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(20)

$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(22)

$306.3

/ Nightly
Private Vacation Home

Woods & Windows - Treehouse for Adults - Near a Lake, Waterfall and Tanglewood!

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(12)

$448.03

/ 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(4)

$454.47

/ Nightly
Private Vacation Home

Mac Shores | 5 min to Tanglewood ! • Shared Beach

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(2)

$459.6

/ 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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$488.52

/ Nightly
Private Vacation Home

Stockbridge In-town Escape

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(6)

$496.88

/ Nightly
Private Vacation Home

Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$535.2

/ Nightly
Private Vacation Home

Charming cottage in Norman Rockwell's Stockbridge with two decks!

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(21)

$548.14

/ Nightly
Private Vacation Home

Classic Stockbridge Cottage

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$568.69

/ Nightly
Private Vacation Home

Fall Weekends and Ski Season is here!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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View 38 Private vacation home

Home Most popular vacation rentals in Stockbridge

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Exceptional(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$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(1)

$320.47

/ Nightly
Cottage

Cozy Winter Retreat

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

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