Vacation Rentals By Owner In Great Barrington, MA

Showing 100 Of 122 Vacation Rentals

Exceptional(59)

$585.31

/ Nightly

Private Vacation Home

Minutes from downtown Great Barrington, Convenient location

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$554.74

/ Nightly

Private Vacation Home

Prime Location, Recently Redesigned, Riverfront!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$1078.39

/ Nightly

Private Vacation Home

Luxury Retreat Minutes from Great Barrington & Ski Slopes

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(16)

$282.79

/ Nightly

Cabin

Steps to Lake Buel, close to Great Barrington & Stockbridge

Monterey, Massachusetts, United States

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Bath

Sleeps

Exceptional(10)

$1400.8

/ Nightly

Private Vacation Home

Berkshires Estate w/ Heated Pool by Evergreen Home

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(3)

$551.52

/ Nightly

Private Vacation Home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

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Bath

Sleeps

$550.46

/ Nightly

Private Vacation Home

1840 Village Farmhouse with Modern Comforts

Egremont, Massachusetts, United States

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Bath

Sleeps

$723.07

/ Nightly

Cottage

Charming historic country cottage on 7 private acres near Tanglewood & skiing

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(54)

$2328.39

/ Nightly

Lodge

Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(6)

$535.43

/ Nightly

Private Vacation Home

The Summerwood Hideout | Mins to Downtown! • Pool

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(14)

$391.32

/ Nightly

Apartment

Zen Riverfront studio w/ Spa steam shower, wood stove, SKI Catamount /Butternut

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(9)

$540.33

/ Nightly

Private Vacation Home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$11202.62

/ Nightly

Cabin

Charming Cabin On Scenic Road

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(52)

$462.44

/ Nightly

Private Vacation Home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(53)

$1254.39

/ Nightly

Private Vacation Home

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(26)

$889.67

/ Nightly

Private Vacation Home

Massachusetts Lake House w/ Dock - Pets Welcome!

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$674.73

/ Nightly

Private Vacation Home

Sunsets On Blue Hill, Newly Renovated Farmhouse

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(22)

$587.54

/ Nightly

Private Vacation Home

Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$643.31

/ Nightly

Private Vacation Home

Renovated Downtown Great Barrington House

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

Select Dates for Price

Private Vacation Home

Family Home With Big Yard On The Hill, Short Walk To Downtown And Lake Mansfield

Great Barrington, Massachusetts, United States

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Bath

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Rent a place that suits your needs

Private vacation home

View 99 Private vacation home

Most popular vacation rentals in Great Barrington

Exceptional(18)

$551.52

/ Nightly

Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(18)

$462.44

/ Nightly

Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$491.48

/ Nightly

Private vacation home

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$519.78

/ Nightly

Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$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

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Bath

Sleeps

Exceptional(18)

$538.86

/ Nightly

Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$540.33

/ Nightly

Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$544.83

/ Nightly

Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$570.23

/ Nightly

Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(18)

$569.62

/ Nightly

Private vacation home

Catamount, Zip Line, Private Setting, Book Now!

Egremont, Massachusetts, United States

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Bath

Sleeps

Vacation Rentals By Owner In Great Barrington, MA

$585.31

$554.74

$1078.39

$282.79

$1400.8

$551.52

$550.46

$723.07

$2328.39

$535.43

$391.32

$540.33

$11202.62

$462.44

$1254.39

$889.67

$674.73

$587.54

$643.31

Rent a place that suits your needs

Most popular vacation rentals in Great Barrington

$551.52

$462.44

$491.48

$519.78

$536.16

$538.86

$540.33

$544.83

$570.23

$569.62

Most Popular Cities in Massachusetts