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Holiday Rentals in Great Barrington

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
82 rentals in Great Barrington.
Modern Cottage Minutes from Downtown  Great Barrington, holiday rental in Great Barrington
Modern Cottage Minutes from Downtown  Great Barrington, holiday rental in Great Barrington
Modern Cottage Minutes from Downtown  Great Barrington, holiday rental in Great Barrington

Modern Cottage Minutes from Downtown Great Barrington

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi, holiday rental in Great Barrington
Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi, holiday rental in Great Barrington
Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi, holiday rental in Great Barrington

Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, holiday rental in Great Barrington
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, holiday rental in Great Barrington
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, holiday rental in Great Barrington

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful House In The Woods, Huge Yard, Hot Tub, holiday rental in Great Barrington
Beautiful House In The Woods, Huge Yard, Hot Tub, holiday rental in Great Barrington
Beautiful House In The Woods, Huge Yard, Hot Tub, holiday rental in Great Barrington

Beautiful House In The Woods, Huge Yard, Hot Tub

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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A perfect getaway year-round.  Booking for the rest of '23 and through '24!, holiday rental in Great Barrington
A perfect getaway year-round.  Booking for the rest of '23 and through '24!, holiday rental in Great Barrington
A perfect getaway year-round.  Booking for the rest of '23 and through '24!, holiday rental in Great Barrington

A perfect getaway year-round. Booking for the rest of '23 and through '24!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Peaceful Retreat Compound 10 Minutes to Great Barrington!, holiday rental in Great Barrington
Peaceful Retreat Compound 10 Minutes to Great Barrington!, holiday rental in Great Barrington
Peaceful Retreat Compound 10 Minutes to Great Barrington!, holiday rental in Great Barrington

Peaceful Retreat Compound 10 Minutes to Great Barrington!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Historic 4-bedroom riverside home in Berkshires, holiday rental in Great Barrington
Historic 4-bedroom riverside home in Berkshires, holiday rental in Great Barrington
Historic 4-bedroom riverside home in Berkshires, holiday rental in Great Barrington

Historic 4-bedroom riverside home in Berkshires

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Home in Great Barrington, holiday rental in Great Barrington
Home in Great Barrington, holiday rental in Great Barrington
Home in Great Barrington, holiday rental in Great Barrington

Home in Great Barrington

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Modern Victorian Walk to Town, holiday rental in Great Barrington
Modern Victorian Walk to Town, holiday rental in Great Barrington
Modern Victorian Walk to Town, holiday rental in Great Barrington

Modern Victorian Walk to Town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stay in Town, Enjoy Late Check Out, holiday rental in Great Barrington
Stay in Town, Enjoy Late Check Out, holiday rental in Great Barrington
Stay in Town, Enjoy Late Check Out, holiday rental in Great Barrington

Stay in Town, Enjoy Late Check Out

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Great Escape Ski Cottage w/HOT TUB * Great Barrington, holiday rental in Great Barrington
The Great Escape Ski Cottage w/HOT TUB * Great Barrington, holiday rental in Great Barrington
The Great Escape Ski Cottage w/HOT TUB * Great Barrington, holiday rental in Great Barrington

The Great Escape Ski Cottage w/HOT TUB * Great Barrington

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Stunning Renovated Victorian, holiday rental in Great Barrington
Stunning Renovated Victorian, holiday rental in Great Barrington
Stunning Renovated Victorian, holiday rental in Great Barrington

Stunning Renovated Victorian

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Morgan's Millhouse (Front), holiday rental in Great Barrington
Morgan's Millhouse (Front), holiday rental in Great Barrington
Morgan's Millhouse (Front), holiday rental in Great Barrington

Morgan's Millhouse (Front)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great escape Barrington, holiday rental in Great Barrington
Great escape Barrington, holiday rental in Great Barrington
Great escape Barrington, holiday rental in Great Barrington

Great escape Barrington

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington, holiday rental in Great Barrington
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington, holiday rental in Great Barrington
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington, holiday rental in Great Barrington

Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
More info
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Great Barrington, Cabin Sleeps 14, Walk To Town, holiday rental in Great Barrington
Great Barrington, Cabin Sleeps 14, Walk To Town, holiday rental in Great Barrington
Great Barrington, Cabin Sleeps 14, Walk To Town, holiday rental in Great Barrington

Great Barrington, Cabin Sleeps 14, Walk To Town

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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In-town studio apartment. Great base for a Berkshire visit!, holiday rental in Great Barrington
In-town studio apartment. Great base for a Berkshire visit!, holiday rental in Great Barrington
In-town studio apartment. Great base for a Berkshire visit!, holiday rental in Great Barrington

In-town studio apartment. Great base for a Berkshire visit!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Charming Cabin On Scenic Road, holiday rental in Great Barrington
Charming Cabin On Scenic Road, holiday rental in Great Barrington
Charming Cabin On Scenic Road, holiday rental in Great Barrington

Charming Cabin On Scenic Road

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Serene Renovated Barn w/ Firepit, holiday rental in Great Barrington
Serene Renovated Barn w/ Firepit, holiday rental in Great Barrington
Serene Renovated Barn w/ Firepit, holiday rental in Great Barrington

Serene Renovated Barn w/ Firepit

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Berkshires: Romantic Cottage with spectacular view, holiday rental in Great Barrington
Berkshires: Romantic Cottage with spectacular view, holiday rental in Great Barrington
Berkshires: Romantic Cottage with spectacular view, holiday rental in Great Barrington

Berkshires: Romantic Cottage with spectacular view

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Payment Protection
Romantic Berkshires Cottage - Stunning Views, Pool, holiday rental in Great Barrington
Romantic Berkshires Cottage - Stunning Views, Pool, holiday rental in Great Barrington
Romantic Berkshires Cottage - Stunning Views, Pool, holiday rental in Great Barrington

Romantic Berkshires Cottage - Stunning Views, Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Studio Loft in the Berkshires, holiday rental in Great Barrington
Studio Loft in the Berkshires, holiday rental in Great Barrington
Studio Loft in the Berkshires, holiday rental in Great Barrington

Studio Loft in the Berkshires

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington
Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington
Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington

Apartment in Gorgeous Stonybrook Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Evergreen: quiet cottage in Great Barrington, holiday rental in Great Barrington
Evergreen: quiet cottage in Great Barrington, holiday rental in Great Barrington
Evergreen: quiet cottage in Great Barrington, holiday rental in Great Barrington

Evergreen: quiet cottage in Great Barrington

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Eastbungalow, holiday rental in Great Barrington
Eastbungalow, holiday rental in Great Barrington
Eastbungalow, holiday rental in Great Barrington

Eastbungalow

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Lake Community - Near Town, Attractions, holiday rental in Great Barrington
Lake Community - Near Town, Attractions, holiday rental in Great Barrington
Lake Community - Near Town, Attractions, holiday rental in Great Barrington

Lake Community - Near Town, Attractions

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Best of the Berkshires + Hot Tub!, holiday rental in Great Barrington
Best of the Berkshires + Hot Tub!, holiday rental in Great Barrington
Best of the Berkshires + Hot Tub!, holiday rental in Great Barrington

Best of the Berkshires + Hot Tub!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Berkshire Mountain Cottage: in the Heart of the Berkshires, holiday rental in Great Barrington
Berkshire Mountain Cottage: in the Heart of the Berkshires, holiday rental in Great Barrington
Berkshire Mountain Cottage: in the Heart of the Berkshires, holiday rental in Great Barrington

Berkshire Mountain Cottage: in the Heart of the Berkshires

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Entire home hosted by Morgan, holiday rental in Great Barrington
Entire home hosted by Morgan, holiday rental in Great Barrington
Entire home hosted by Morgan, holiday rental in Great Barrington

Entire home hosted by Morgan

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Great Barrington
2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Great Barrington
2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Great Barrington

2 bedroom Riverhouse in the Heart of the Berkshires

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Potential Ski Season Rental - Buttuernut/Catamount, holiday rental in Great Barrington
Potential Ski Season Rental - Buttuernut/Catamount, holiday rental in Great Barrington
Potential Ski Season Rental - Buttuernut/Catamount, holiday rental in Great Barrington

Potential Ski Season Rental - Buttuernut/Catamount

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great Barrington Guest House, Newly Renovated!, holiday rental in Great Barrington
Great Barrington Guest House, Newly Renovated!, holiday rental in Great Barrington
Great Barrington Guest House, Newly Renovated!, holiday rental in Great Barrington

Great Barrington Guest House, Newly Renovated!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Modern Riverside Cottage in Hip Walkable Community, holiday rental in Great Barrington
Modern Riverside Cottage in Hip Walkable Community, holiday rental in Great Barrington
Modern Riverside Cottage in Hip Walkable Community, holiday rental in Great Barrington

Modern Riverside Cottage in Hip Walkable Community

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Idyllic Berkshire Get Away: Balance of relaxation and convenience, holiday rental in Great Barrington
Idyllic Berkshire Get Away: Balance of relaxation and convenience, holiday rental in Great Barrington
Idyllic Berkshire Get Away: Balance of relaxation and convenience, holiday rental in Great Barrington

Idyllic Berkshire Get Away: Balance of relaxation and convenience

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Great Barrington Farmhouse near Lake Mansfield, holiday rental in Great Barrington
Great Barrington Farmhouse near Lake Mansfield, holiday rental in Great Barrington
Great Barrington Farmhouse near Lake Mansfield, holiday rental in Great Barrington

Great Barrington Farmhouse near Lake Mansfield

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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Renovated Downtown Great Barrington House, holiday rental in Great Barrington
Renovated Downtown Great Barrington House, holiday rental in Great Barrington
Renovated Downtown Great Barrington House, holiday rental in Great Barrington

Renovated Downtown Great Barrington House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Great Barrington Walkable To Lake And Town!, holiday rental in Great Barrington
Great Barrington Walkable To Lake And Town!, holiday rental in Great Barrington
Great Barrington Walkable To Lake And Town!, holiday rental in Great Barrington

Great Barrington Walkable To Lake And Town!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
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Private Home Overlooking Stevens Lake (31 Night Min), holiday rental in Great Barrington
Private Home Overlooking Stevens Lake (31 Night Min), holiday rental in Great Barrington
Private Home Overlooking Stevens Lake (31 Night Min), holiday rental in Great Barrington

Private Home Overlooking Stevens Lake (31 Night Min)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Elegant Lake Buel Home, holiday rental in Great Barrington
Elegant Lake Buel Home, holiday rental in Great Barrington
Elegant Lake Buel Home, holiday rental in Great Barrington

Elegant Lake Buel Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge, holiday rental in Great Barrington
Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge, holiday rental in Great Barrington
Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge, holiday rental in Great Barrington

Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Berkshire Farmhouse Great Barrington Ma, holiday rental in Great Barrington
Charming Berkshire Farmhouse Great Barrington Ma, holiday rental in Great Barrington
Charming Berkshire Farmhouse Great Barrington Ma, holiday rental in Great Barrington

Charming Berkshire Farmhouse Great Barrington Ma

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town, holiday rental in Great Barrington
Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town, holiday rental in Great Barrington
Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town, holiday rental in Great Barrington

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming 1905 Mill House, secluded, yet walking distance to Main Street stores,., holiday rental in Great Barrington
Charming 1905 Mill House, secluded, yet walking distance to Main Street stores,., holiday rental in Great Barrington
Charming 1905 Mill House, secluded, yet walking distance to Main Street stores,., holiday rental in Great Barrington

Charming 1905 Mill House, secluded, yet walking distance to Main Street stores,.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Remodeled ski and summer retreat close to town, holiday rental in Great Barrington
Remodeled ski and summer retreat close to town, holiday rental in Great Barrington
Remodeled ski and summer retreat close to town, holiday rental in Great Barrington

Remodeled ski and summer retreat close to town

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Great Barrington Home ~ 1 Mi to Ski Resort!, holiday rental in Great Barrington
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!, holiday rental in Great Barrington
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!, holiday rental in Great Barrington

Cozy Great Barrington Home ~ 1 Mi to Ski Resort!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Renovated house on the Hill.  Walk everywhere!, holiday rental in Great Barrington
Renovated house on the Hill.  Walk everywhere!, holiday rental in Great Barrington
Renovated house on the Hill.  Walk everywhere!, holiday rental in Great Barrington

Renovated house on the Hill. Walk everywhere!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard, holiday rental in Great Barrington
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard, holiday rental in Great Barrington
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard, holiday rental in Great Barrington

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Classic Berkshires cottage in sun-drenched meadow, holiday rental in Great Barrington
Classic Berkshires cottage in sun-drenched meadow, holiday rental in Great Barrington
Classic Berkshires cottage in sun-drenched meadow, holiday rental in Great Barrington

Classic Berkshires cottage in sun-drenched meadow

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Berkshires Getaway Minutes to Ski Butternut, holiday rental in Great Barrington
Private Berkshires Getaway Minutes to Ski Butternut, holiday rental in Great Barrington
Private Berkshires Getaway Minutes to Ski Butternut, holiday rental in Great Barrington

Private Berkshires Getaway Minutes to Ski Butternut

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Minutes from downtown Great Barrington, Convenient location, holiday rental in Great Barrington
Minutes from downtown Great Barrington, Convenient location, holiday rental in Great Barrington
Minutes from downtown Great Barrington, Convenient location, holiday rental in Great Barrington

Minutes from downtown Great Barrington, Convenient location

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-50 of 82
Frequently Asked Questions about Great Barrington