Vacation Rentals By Owner In Great Barrington, MA

Showing 120 Of 122 Vacation Rentals

Exceptional(1)

$1851.34

/ Nightly

Private Vacation Home

Rosecliff: Ultra-Lux Pool, Big Views, Green River, Sleeps 15

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(39)

$335.1

/ Nightly

Private Vacation Home

Home in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(143)

$584.94

/ Nightly

Private Vacation Home

5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$832.32

/ Nightly

Private Vacation Home

Chic, Mid Century 3+ Bedroom with Hot Tub!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$548.12

/ Nightly

Private Vacation Home

Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1004.3

/ Nightly

Private Vacation Home

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

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$899.76

/ Nightly

Private Vacation Home

Fireplace, Privacy, Screen Porch, 1 Level Living!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$918.03

/ Nightly

Private Vacation Home

Light-filled, Stylish, Farmhouse Colonial, Egremont MA

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$753.99

/ Nightly

Private Vacation Home

Fall Weekends: Hot Tub, Green River Hike, Sleeps 10

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$403.7

/ Nightly

Private Vacation Home

Picturesque cottage house with nearby lake and cafe

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Exceptional(17)

$562.22

/ Nightly

Private Vacation Home

Log style home 4 miles to Catamount with fitness room

Egremont, Massachusetts, United States

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Bath

Sleeps

Exceptional(11)

$495.76

/ Nightly

Private Vacation Home

Family vacation home in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$403.58

/ Nightly

Private Vacation Home

Farmhouse with views nestled among nature reserve

Great Barrington, Massachusetts, United States

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Bath

Sleeps

Exceptional(2)

$4952.9

/ Nightly

Private Vacation Home

Sunset Falls Estate: 167-acre mountain home, indoor sauna, cold plunge & steam

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Exceptional(78)

$303.87

/ Nightly

Cottage

Charming Cottage, New Marlborough Village Green in the Berkshires

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(67)

$401.01

/ Nightly

Cottage

Romantic Berkshires Cottage - Stunning Views, Pool

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$559.83

/ Nightly

Private Vacation Home

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$1160.83

/ Nightly

Private Vacation Home

Fernbrook - Contemporary Getaway with Private Home Gym near Great Barrington

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$584.96

/ Nightly

Private Vacation Home

Hot Tub, Chic Sexy Style booking Summer 26!

New Marlborough, Massachusetts, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 99 Private vacation home

Most popular vacation rentals in Great Barrington

$551.52

/ Nightly

Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$462.44

/ Nightly

Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

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Bath

Sleeps

$491.48

/ Nightly

Private vacation home

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$519.78

/ Nightly

Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$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

$538.86

/ Nightly

Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$540.33

/ Nightly

Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$544.83

/ Nightly

Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$570.23

/ Nightly

Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$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

$1851.34

$335.1

$584.94

$832.32

$548.12

$1004.3

$899.76

$918.03

$753.99

$403.7

$562.22

$495.76

$403.58

$4952.9

$303.87

$975.09

$401.01

$559.83

$1160.83

$584.96

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