Vacation Rentals By Owner In Great Barrington, MA

Showing 20 Of 122 Vacation Rentals

Exceptional(40)

$517.17

/ Nightly

Private Vacation Home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$230.77

/ Nightly

Apartment

The Serendipity Spot

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(11)

$855.07

/ Nightly

Private Vacation Home

Berkshires / Great Barrington Chic & Cozy, Sleeps 10

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$566.42

/ Nightly

Private Vacation Home

Screened Porch, Sun Deck, Spotless, GB Center!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(11)

$613.79

/ Nightly

Private Vacation Home

Butternut Ski Retreat - Fireplace, Views and close to town!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$834.57

/ Nightly

Private Vacation Home

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

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$360.98

/ Nightly

Apartment

New Listing!! Berkshire Flat Overlooking Rising Pond!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$362.18

/ Nightly

Cabin

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1433.12

/ Nightly

Private Vacation Home

Berkshire Bliss: Nature + Luxe

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(16)

$1811.55

/ Nightly

Private Vacation Home

Swim All Day. Stroll to Dinner. Repeat.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$874.31

/ Nightly

Private Vacation Home

Cozy escape in the trees of the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$342.36

/ Nightly

Private Vacation Home

Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

$155.86

/ Nightly

Private Vacation Home

Cozy River Spot in a Quaint New England Village

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$1702.55

/ Nightly

Private Vacation Home

Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$918.03

/ Nightly

Private Vacation Home

Mountain Views, Playroom, Fireplaces, Sleeps 8+!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$830.72

/ Nightly

Private Vacation Home

Fall Weekends, Lake Buel Dock Sunsets: Sleeps 8!

Monterey, Massachusetts, United States

Bed

Bath

Sleeps

$1017.71

/ Nightly

Private Vacation Home

Woodland - Stunning 5 bedroom home in GB!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$139.63

/ Nightly

Apartment

Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$319.77

/ Nightly

Cottage

2-bedroom cottage close to hiking and swimming with AC

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$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

Rent a place that suits your needs

Private vacation home

View 99 Private vacation home

Most popular vacation rentals in Great Barrington

Exceptional(3)

$551.52

/ Nightly

Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$462.44

/ Nightly

Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$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(3)

$519.78

/ Nightly

Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$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(3)

$538.86

/ Nightly

Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$540.33

/ Nightly

Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$544.83

/ Nightly

Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$570.23

/ Nightly

Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$569.62

/ Nightly

Private vacation home

Catamount, Zip Line, Private Setting, Book Now!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Great Barrington, MA

$517.17

$230.77

$855.07

$566.42

$613.79

$834.57

$360.98

$362.18

$1433.12

$1811.55

$874.31

$342.36

$155.86

$1702.55

$918.03

$830.72

$1017.71

$139.63

$319.77

$536.16

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