Vacation Home Rentals By Owner In Great Barrington, MA

Showing 80 Of 99 Vacation Rentals

Exceptional(2)

$434.95

/ Nightly

Private Vacation Home

Jug End Crest | Fireplace • Sunroom • Central Air

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(51)

$431.16

/ Nightly

Private Vacation Home

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

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(33)

$522.76

/ Nightly

Private Vacation Home

The Hideaway: Berkshire Home - Village of Egremont

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

$403.7

/ Nightly

Private Vacation Home

Picturesque cottage house with nearby lake and cafe

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

$403.58

/ Nightly

Private Vacation Home

Farmhouse with views nestled among nature reserve

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

Exceptional(39)

$335.1

/ Nightly

Private Vacation Home

Home in Great Barrington

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

$333.54

/ Nightly

Private Vacation Home

Great Barrington Farmhouse near Lake Mansfield

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(28)

$316.67

/ Nightly

Private Vacation Home

Leaf-Peeper Paradise in the Berkshires

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$312.69

/ Nightly

Private Vacation Home

The Docent`s House - Honoring a Legacy

Great Barrington, 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

$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

$155.86

/ Nightly

Private Vacation Home

Cozy River Spot in a Quaint New England Village

New Marlborough, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(17)

$562.22

/ Nightly

Private Vacation Home

Log style home 4 miles to Catamount with fitness room

Egremont, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(22)

$587.54

/ Nightly

Private Vacation Home

Great Barrington Lakeside Getaway w/ Kayak & Grill

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(51)

$586.99

/ Nightly

Private Vacation Home

Twin Maple Farm: Charming Modern Farmhouse

Great Barrington, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(59)

$585.31

/ Nightly

Private Vacation Home

Minutes from downtown Great Barrington, Convenient location

Great Barrington, 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

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 Home Rentals By Owner In Great Barrington, MA

$434.95

$431.16

$429.25

$522.76

$407.13

$403.7

$403.58

$342.36

$335.1

$333.54

$316.67

$312.69

$285.38

$212.28

$155.86

$562.22

$587.54

$586.99

$585.31

$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