Home Vacation Rentals By Owner In Stockbridge, MA

Showing 20 Of 55 Vacation Rentals
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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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$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(19)

$345.9

/ Nightly
Cabin

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 2

Bath

Sleep 4

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(6)

$195

/ Nightly
Condo

Summer in the Berkshires!

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 7

Sleeps
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Exceptional(5)

Select Dates for Price
Apartment

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

Stockbridge, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

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(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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Exceptional(6)

$468.58

/ 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(10)

$243.79

/ Nightly
Cottage

Light-filled Carpenter's Cottage w/ EV charger!

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

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(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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$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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$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(22)

$356.32

/ Nightly
Cabin

Artist's Camp on Lake Mahkeenac

Stockbridge, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

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(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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Exceptional(1)

$479.63

/ Nightly
Cottage

Grandparent’s Cottage 250 steps to the lake

Stockbridge, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 7

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(15)

$324.83

/ Nightly
Cottage

Cozy Winter Retreat

Stockbridge, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Private vacation home

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View 38 Private vacation home

Home Most popular vacation rentals in Stockbridge

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Exceptional(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(15)

$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(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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Exceptional(15)

$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(15)

$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