Vacation Rentals By Owner In Great Barrington, MA

Showing 40 Of 122 Vacation Rentals

Exceptional(51)

$431.16

/ Nightly

Private Vacation Home

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$112.73

/ Nightly

Cabin

Log Cabin in the Woods with a Rustic Vibe

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(10)

$569.62

/ Nightly

Private Vacation Home

Catamount, Zip Line, Private Setting, Book Now!

Egremont, 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(3)

$577.68

/ Nightly

Private Vacation Home

New England Family Home with Hot Tub and Pool

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$212.28

/ Nightly

Private Vacation Home

Large 3-bedroom house with WiFi and AC in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$1306.12

/ Nightly

Private Vacation Home

Serene 5-BR Retreat 9-Min to Catamount

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(62)

$204.41

/ Nightly

Apartment

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(61)

$1301.79

/ Nightly

Private Vacation Home

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(38)

$694.52

/ Nightly

Private Vacation Home

Private Woodland Getaway minutes from Ski Butternut

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$285.38

/ Nightly

Private Vacation Home

Timeless Enchanting Egremont Cottage: Delight the Senses!

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$701.85

/ Nightly

Private Vacation Home

3-Bedroom Victorian home within walking distance of downtown Great Barrington.

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$853

/ Nightly

Private Vacation Home

Spacious 5-bedroom house in Egremont with AC and POOL

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$616.31

/ Nightly

Private Vacation Home

Perfect Nature Haven In Great Barrington

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

$631.63

/ Nightly

Private Vacation Home

Chalet in Great Barrington near 2 Ski Areas

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$742.72

/ Nightly

Private Vacation Home

River Cottage - Riverfront Home in Walkable Community

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$679.76

/ Nightly

Private Vacation Home

Steepletop - Nature Lovers Paradise with Rec Room

New Marlborough, 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

$516.05

/ Nightly

Private Vacation Home

Heated Pool & Hot Tub • Ideal Berkshires / Hudson Valley 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

$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

Bed

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

Bed

Bath

Sleeps

Vacation Rentals By Owner In Great Barrington, MA

$431.16

$112.73

$569.62

$491.48

$577.68

$212.28

$1306.12

$204.41

$1301.79

$694.52

$285.38

$701.85

$853

$616.31

$513.55

$631.63

$742.72

$679.76

$538.86

$516.05

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