Vacation Home Rentals By Owner In Great Barrington, MA

Showing 60 Of 99 Vacation Rentals

$1160.83

/ Nightly

Private Vacation Home

Fernbrook - Contemporary Getaway with Private Home Gym near Great Barrington

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(62)

$1140.09

/ Nightly

Private Vacation Home

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

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(37)

$1044.96

/ Nightly

Private Vacation Home

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$1017.71

/ Nightly

Private Vacation Home

Woodland - Stunning 5 bedroom home in GB!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$1004.3

/ Nightly

Private Vacation Home

5 Stars w/ Hot Tub, Sunny Patio, Game Room, Views!

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(12)

$999.99

/ Nightly

Private Vacation Home

Lake Buel Waterfront - 4 Bedrooms with private dock

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Exceptional(43)

$975.09

/ Nightly

Private Vacation Home

Jaw dropping mountain & lake views in this stylish mountain home….

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(8)

$964.4

/ Nightly

Private Vacation Home

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(5)

$960.7

/ Nightly

Private Vacation Home

Private Country Estate: Heated Pool, Sleeps 20

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(5)

$423

/ Nightly

Private Vacation Home

Gilbert Ski Chalet | 3 min to Catamount!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$521.08

/ Nightly

Private Vacation Home

Private Home in the Berkshires with Hot Tub

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(40)

$517.17

/ Nightly

Private Vacation Home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$516.05

/ Nightly

Private Vacation Home

Heated Pool & Hot Tub • Ideal Berkshires / Hudson Valley Getaway

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$513.55

/ Nightly

Private Vacation Home

Light-Filled GB Oasis, Trails, Lake, Fireplace

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(11)

$495.76

/ Nightly

Private Vacation Home

Family vacation home in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(37)

$491.48

/ Nightly

Private Vacation Home

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(52)

$462.44

/ Nightly

Private Vacation Home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$453.12

/ Nightly

Private Vacation Home

Nature Retreat Near Prospect Lake

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$440.1

/ Nightly

Private Vacation Home

Tranquil 2-bedroom house with woodland and pasture views in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 99 Private vacation home

Most popular vacation rentals in Great Barrington

Exceptional(6)

$551.52

/ Nightly

Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$462.44

/ Nightly

Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$491.48

/ Nightly

Private vacation home

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$519.78

/ Nightly

Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$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

Bath

Sleeps

Exceptional(6)

$538.86

/ Nightly

Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$540.33

/ Nightly

Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$544.83

/ Nightly

Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$570.23

/ Nightly

Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$569.62

/ Nightly

Private vacation home

Catamount, Zip Line, Private Setting, Book Now!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Great Barrington, MA

$1160.83

$1140.09

$1078.39

$1044.96

$1017.71

$1004.3

$999.99

$975.09

$964.4

$960.7

$423

$521.08

$517.17

$516.05

$513.55

$495.76

$491.48

$462.44

$453.12

$440.1

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