Vacation Rentals By Owner In Great Barrington, MA

Showing 60 Of 122 Vacation Rentals

$1169.17

/ Nightly

Private Vacation Home

The Novogratz - Artsy, Heated Pool + Hot Tub!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$895.24

/ Nightly

Private Vacation Home

Expansive Berkshire Retreat with Pool and Hot Tub and Sleeps 18

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(27)

$407.13

/ Nightly

Private Vacation Home

Peaceful, Post and Beam Loft, Sleeps 9

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(5)

$867.46

/ Nightly

Private Vacation Home

Beautiful Berkshires Fall Foliage Retreat

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$273.94

/ Nightly

Apartment

Fabulous Apartment - Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$169.73

/ Nightly

Apartment

Charming 2-bedroom apartment in Great Barrington, set in nature.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(54)

$552.28

/ Nightly

Private Vacation Home

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(13)

$544.83

/ Nightly

Private Vacation Home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(48)

$298.02

/ Nightly

Cottage

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough, Massachusetts, United States

Bed

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(1)

$453.12

/ Nightly

Private Vacation Home

Nature Retreat Near Prospect Lake

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(12)

$999.99

/ Nightly

Private Vacation Home

Lake Buel Waterfront - 4 Bedrooms with private dock

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(60)

$1690.58

/ Nightly

Private Vacation Home

Stunning Renovated Victorian

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$196.36

/ Nightly

Guest House

Renovated Private Guest House by Evergreen Home

Great Barrington, 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

Exceptional(13)

$429.25

/ Nightly

Private Vacation Home

Timberdoodle-a mountainside retreat

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(43)

$573.03

/ Nightly

Private Vacation Home

An In-Town Beauty with Late Checkout

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$434.95

/ Nightly

Private Vacation Home

Jug End Crest | Fireplace • Sunroom • Central Air

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$1339.59

/ Nightly

Private Vacation Home

Renovated family friendly house close to everything and endless views

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$566.88

/ Nightly

Private Vacation Home

Modern Victorian Walk to Main Street

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(29)

$551.52

/ Nightly

Private vacation home

Hilltop Escape with Views & Hot Tub

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$462.44

/ Nightly

Private vacation home

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$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(29)

$519.78

/ Nightly

Private vacation home

A Fun Farmhouse Near Ski Butternut

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$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(29)

$538.86

/ Nightly

Private vacation home

Meadow Top Cottage: Countryside Cottage on 72 Acres

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$540.33

/ Nightly

Private vacation home

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$544.83

/ Nightly

Private vacation home

Modern Escape Near Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$570.23

/ Nightly

Private vacation home

Modern Victorian Walk to Main Street

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(29)

$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

$1169.17

$895.24

$407.13

$867.46

$273.94

$169.73

$552.28

$544.83

$298.02

$960.7

$453.12

$999.99

$1690.58

$196.36

$440.1

$429.25

$573.03

$434.95

$1339.59

$566.88

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