Home Vacation Home Rentals By Owner In Great Barrington, MA

Showing 99 Of 99 Vacation Rentals
Slider Thumb
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 5

Bed

Bath 3

Bath

Sleep 12

Sleeps
Slider Thumb
Exceptional(7)

$581.95

/ Nightly
Private Vacation Home

Outdoor Sauna, Hot tub, Fire Pit, Dogs Welcome!

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(3)

$577.68

/ Nightly
Private Vacation Home

New England Family Home with Hot Tub and Pool

New Marlborough, Massachusetts, United States

Bed 5

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(43)

$573.03

/ Nightly
Private Vacation Home

An In-Town Beauty with Late Checkout

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(10)

$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
Slider Thumb
Exceptional(29)

$566.88

/ Nightly
Private Vacation Home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps
Slider Thumb

$566.42

/ Nightly
Private Vacation Home

Screened Porch, Sun Deck, Spotless, GB Center!

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
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

Bed 4

Bed

Bath 2

Bath

Sleep 10

Sleeps
Slider Thumb
Exceptional(2)

$559.83

/ Nightly
Private Vacation Home

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

Egremont, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(1)

$554.74

/ Nightly
Private Vacation Home

Prime Location, Recently Redesigned, Riverfront!

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(54)

$552.28

/ Nightly
Private Vacation Home

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 14

Sleeps
Slider Thumb
Exceptional(3)

$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
Slider Thumb

$550.46

/ Nightly
Private Vacation Home

1840 Village Farmhouse with Modern Comforts

Egremont, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
Slider Thumb

$548.12

/ Nightly
Private Vacation Home

Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Great Barrington, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

Sleeps
Slider Thumb
Exceptional(13)

$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
Slider Thumb
Exceptional(9)

$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
Slider Thumb
Exceptional(3)

$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
Slider Thumb
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 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(6)

$535.43

/ Nightly
Private Vacation Home

The Summerwood Hideout | Mins to Downtown! • Pool

Great Barrington, Massachusetts, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

Sleeps
map-loader

Home Rent a place that suits your needs

Private vacation home

Private vacation home

View 99 Private vacation home

Home Most popular vacation rentals in Great Barrington

Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
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 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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
Slider Thumb
Exceptional(6)

$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