Great Barrington, Massachusetts

Vacation Rentals in Great Barrington, Massachusetts

Discover 23 vacation rental properties in Great Barrington. From 1 to 5 bedrooms. Average $439/night. 100% have pools.

23 verified listings Book securely on VRBO Prices updated March 2026

23 properties available

Romantic Berkshires Cottage - Stunning Views, Pool

Romantic Berkshires Cottage - Stunning Views, Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$239/night
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Apartment in Gorgeous Stonybrook Farm

Apartment in Gorgeous Stonybrook Farm

1 bed 1 bath
PoolA/CWiFiBalcony
$160/night
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Home in Great Barrington

Home in Great Barrington

2 beds 1 bath
PoolA/CWiFiBalcony
$288/night
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Beautiful House In The Woods, Huge Yard, Hot Tub

Beautiful House In The Woods, Huge Yard, Hot Tub

4 beds 3 baths
PoolA/CWiFiBalcony
$596/night
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Log style home 4 miles to Catamount with fitness room

Log style home 4 miles to Catamount with fitness room

4 beds 3 baths
PoolA/CWiFiBalcony
$359/night
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NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

3 beds 3 baths
PoolA/CWiFiBalcony
$395/night
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Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

3 beds 3 baths
PoolA/CWiFiBalcony
$419/night
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Peaceful Retreat Compound 10 Minutes to Great Barrington!

Peaceful Retreat Compound 10 Minutes to Great Barrington!

4 beds 3 baths
PoolA/CWiFiBalcony
$1,469/night
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

4 beds 2 baths
PoolA/CWiFiBalcony
$329/night
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Idyllic Berkshire Get Away: Balance of relaxation and convenience

Idyllic Berkshire Get Away: Balance of relaxation and convenience

3 beds 2 baths
PoolA/CWiFiBalcony
$287/night
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Great Barrington Getaway: Lake Access, Water Views

Great Barrington Getaway: Lake Access, Water Views

3 beds 2 baths
PoolA/CWiFiBalcony
$335/night
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Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB

Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB

3 beds 2 baths
PoolA/CWiFiBalcony
$445/night
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Modern Cottage Minutes from Downtown Great Barrington

Modern Cottage Minutes from Downtown Great Barrington

4 beds 3 baths
PoolA/CWiFiBalcony
$568/night
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Great Barrington Get Away

Great Barrington Get Away

3 beds 2 baths
PoolA/CWiFiBalcony
$343/night
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Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town

3 beds 2 baths
PoolA/CWiFiBalcony
$486/night
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Great Barrington Walkable to Lake and Town!

Great Barrington Walkable to Lake and Town!

3 beds 2 baths
PoolA/CWiFiBalcony
$324/night
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Twin Maple Farm: Charming Modern Farmhouse

Twin Maple Farm: Charming Modern Farmhouse

4 beds 2 baths
PoolA/CWiFiBalcony
$328/night
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Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town

Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town

3 beds 2 baths
PoolA/CWiFiBalcony
$522/night
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Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

3 beds 2 baths
PoolA/CWiFiBalcony
$410/night
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Renovated Private Guest House by Evergreen Home

Renovated Private Guest House by Evergreen Home

2 beds 1 bath
PoolA/CWiFiBalcony
$140/night
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Berkshires Estate w/ Heated Pool by Evergreen Home

Berkshires Estate w/ Heated Pool by Evergreen Home

5 beds 4 baths
PoolA/CWiFiBalcony
$946/night
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Family vacation home in Great Barrington

Family vacation home in Great Barrington

4 beds 3 baths
PoolA/CWiFiBalcony
$344/night
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Historic 4-bedroom riverside home in Berkshires

Historic 4-bedroom riverside home in Berkshires

4 beds 2 baths
PoolA/CWiFiBalcony
$361/night
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More destinations in Massachusetts

Boston (1034) Nantucket (637) Provincetown (428) Falmouth (348) Wellfleet (288) Cambridge (276) Brewster (271) Chatham (258) Plymouth (247) Gloucester (203) Yarmouth (164) Sandwich (163) Rockport (158) Barnstable (155) Eastham (143) Dennis (139) Dennis Port (129) North Truro (126) Hyannis (121) South Yarmouth (115)