Home Vacation Home Rentals By Owner In Great Barrington, MA

Showing 20 Of 99 Vacation Rentals
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$834.57

/ Nightly
Private Vacation Home

Heated Pool (closes 10/13) Sun Room, Privacy!

New Marlborough, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(3)

$709.29

/ Nightly
Private Vacation Home

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$674.73

/ Nightly
Private Vacation Home

Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(2)

$668.61

/ Nightly
Private Vacation Home

Historic, Modern Comforts, Walk To Downtown

Great Barrington, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 16

Sleeps
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Exceptional(2)

$643.31

/ Nightly
Private Vacation Home

Renovated Downtown Great Barrington House

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$631.63

/ Nightly
Private Vacation Home

Chalet in Great Barrington near 2 Ski Areas

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(8)

$616.31

/ Nightly
Private Vacation Home

Perfect Nature Haven In Great Barrington

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(9)

$679.76

/ Nightly
Private Vacation Home

Steepletop - Nature Lovers Paradise with Rec Room

New Marlborough, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$830.72

/ Nightly
Private Vacation Home

Fall Weekends, Lake Buel Dock Sunsets: Sleeps 8!

Monterey, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$832.32

/ Nightly
Private Vacation Home

Chic, Mid Century 3+ Bedroom with Hot Tub!

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(29)

$765.71

/ Nightly
Private Vacation Home

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(2)

$852.65

/ Nightly
Private Vacation Home

Best Berkshire “Readaway” Stay! New reno, stunning private acreage, cultural gem

Egremont, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(1)

$853

/ Nightly
Private Vacation Home

Spacious 5-bedroom house in Egremont with AC and POOL

Egremont, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 9

Sleeps
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Exceptional(11)

$855.07

/ Nightly
Private Vacation Home

Berkshires / Great Barrington Chic & Cozy, Sleeps 10

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Exceptional(5)

$867.46

/ Nightly
Private Vacation Home

Beautiful Berkshires Fall Foliage Retreat

Egremont, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(4)

$874.31

/ Nightly
Private Vacation Home

Cozy escape in the trees of the Berkshires

Great Barrington, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(26)

$889.67

/ Nightly
Private Vacation Home

Massachusetts Lake House w/ Dock - Pets Welcome!

New Marlborough, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(7)

$895.24

/ Nightly
Private Vacation Home

Expansive Berkshire Retreat with Pool and Hot Tub and Sleeps 18

Egremont, Massachusetts, United States

Bed 6

Bed

Bath 6

Bath

Sleep 18

Sleeps
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$899.76

/ Nightly
Private Vacation Home

Fireplace, Privacy, Screen Porch, 1 Level Living!

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 10

Sleeps
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$918.03

/ Nightly
Private Vacation Home

Light-filled, Stylish, Farmhouse Colonial, Egremont MA

Egremont, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
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Home Most popular vacation rentals in Great Barrington

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$551.52

/ Nightly
Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$462.44

/ Nightly
Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 3

Bath

Sleep 6

Sleeps
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$491.48

/ Nightly
Private vacation home

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$519.78

/ Nightly
Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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$536.16

/ Nightly
Private vacation home

Just You, the frozen lake, and 2 nearby ski areas! Perfect cozy winter getaway

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$538.86

/ Nightly
Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$540.33

/ Nightly
Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$544.83

/ Nightly
Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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$570.23

/ Nightly
Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$569.62

/ Nightly
Private vacation home

Catamount, Zip Line, Private Setting, Book Now!

Egremont, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps

Most Popular Cities in Massachusetts