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Holiday Rentals near Housatonic River Walk

195 Main St, Great Barrington, Massachusetts 01230-1602
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Bedrooms

Bathrooms

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Property type

Distinctive Features

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5 mi
71 rentals 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 in Great Barrington

Historic 4-bedroom riverside home in Berkshires

Holiday Rental House
2.0 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
2.1 miles from Housatonic River Walk
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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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
0.6 miles from Housatonic River Walk
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Great Barrington Get Away, holiday rental in Great Barrington
Great Barrington Get Away, holiday rental in Great Barrington
Great Barrington Get Away, holiday rental in Great Barrington

Great Barrington Get Away

Holiday Rental House
0.5 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
0.2 miles from Housatonic River Walk
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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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
0.2 miles from Housatonic River Walk
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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
3.5 miles from Housatonic River Walk
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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
0.2 miles from Housatonic River Walk
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
4.7 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Best of the Berkshires + Hot Tub by Evergreen Home, holiday rental in Great Barrington
Best of the Berkshires + Hot Tub by Evergreen Home, holiday rental in Great Barrington
Best of the Berkshires + Hot Tub by Evergreen Home, holiday rental in Great Barrington

Best of the Berkshires + Hot Tub by Evergreen Home

Holiday Rental House
3.1 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ski Season Rental!, holiday rental in Great Barrington
Ski Season Rental!, holiday rental in Great Barrington
Ski Season Rental!, holiday rental in Great Barrington

Ski Season Rental!

Holiday Rental House
0.2 miles from Housatonic River Walk
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Renovated Private Guest House by Evergreen Home, holiday rental in Great Barrington
Renovated Private Guest House by Evergreen Home, holiday rental in Great Barrington
Renovated Private Guest House by Evergreen Home, holiday rental in Great Barrington

Renovated Private Guest House by Evergreen Home

Holiday Rental House
2.5 miles from Housatonic River Walk
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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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
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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
1.3 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
0.8 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
0.2 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
5.2 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
4.5 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
1.0 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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MacMountain House: Berkshire family retreat, holiday rental in Great Barrington
MacMountain House: Berkshire family retreat, holiday rental in Great Barrington
MacMountain House: Berkshire family retreat, holiday rental in Great Barrington

MacMountain House: Berkshire family retreat

Holiday Rental House
2.1 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Twin Maple Farm: Charming Modern Farmhouse, holiday rental in Great Barrington
Twin Maple Farm: Charming Modern Farmhouse, holiday rental in Great Barrington
Twin Maple Farm: Charming Modern Farmhouse, holiday rental in Great Barrington

Twin Maple Farm: Charming Modern Farmhouse

Holiday Rental House
2.4 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, holiday rental in Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, holiday rental in Great Barrington
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, holiday rental in Great Barrington

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Holiday Rental House
4.1 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family vacation home in Great Barrington, holiday rental in Great Barrington
Family vacation home in Great Barrington, holiday rental in Great Barrington
Family vacation home in Great Barrington, holiday rental in Great Barrington

Family vacation home in Great Barrington

Holiday Rental House
1.6 miles from Housatonic River Walk
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A Fun Farmhouse Near Ski Butternut, holiday rental in Great Barrington
A Fun Farmhouse Near Ski Butternut, holiday rental in Great Barrington
A Fun Farmhouse Near Ski Butternut, holiday rental in Great Barrington

A Fun Farmhouse Near Ski Butternut

Holiday Rental House
1.5 miles from Housatonic River Walk
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Antique Berkshire Farmhouse with heated pool and modern amenities., holiday rental in Great Barrington
Classic Antique Berkshire Farmhouse with heated pool and modern amenities., holiday rental in Great Barrington
Classic Antique Berkshire Farmhouse with heated pool and modern amenities., holiday rental in Great Barrington

Classic Antique Berkshire Farmhouse with heated pool and modern amenities.

Holiday Rental House
2.3 miles from Housatonic River Walk
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home, holiday rental in Great Barrington
Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home, holiday rental in Great Barrington
Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home, holiday rental in Great Barrington

Perfect for Entertaining and Relaxation in the Berkshires!Furnished Country Home

Holiday Rental House
4.7 miles from Housatonic River Walk
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stunning Luxury Berkshire Home with Pool, holiday rental in Great Barrington
Stunning Luxury Berkshire Home with Pool, holiday rental in Great Barrington
Stunning Luxury Berkshire Home with Pool, holiday rental in Great Barrington

Stunning Luxury Berkshire Home with Pool

Holiday Rental House
1.8 miles from Housatonic River Walk
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Great Barrington 4BR home on 3 wooded acres walking distance to town!, holiday rental in Great Barrington
Great Barrington 4BR home on 3 wooded acres walking distance to town!, holiday rental in Great Barrington
Great Barrington 4BR home on 3 wooded acres walking distance to town!, holiday rental in Great Barrington

Great Barrington 4BR home on 3 wooded acres walking distance to town!

Holiday Rental House
0.6 miles from Housatonic River Walk
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Gem of the Berkshires. Mountain View. Short walk to lake & downtown., holiday rental in Great Barrington
Gem of the Berkshires. Mountain View. Short walk to lake & downtown., holiday rental in Great Barrington
Gem of the Berkshires. Mountain View. Short walk to lake & downtown., holiday rental in Great Barrington

Gem of the Berkshires. Mountain View. Short walk to lake & downtown.

Holiday Rental House
0.3 miles from Housatonic River Walk
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
2.6 miles from Housatonic River Walk
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
0.3 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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5 BD, 3 Baths, sleeps 12 -  the pool is open & a few openings for Summer 2024 !, holiday rental in Great Barrington
5 BD, 3 Baths, sleeps 12 -  the pool is open & a few openings for Summer 2024 !, holiday rental in Great Barrington
5 BD, 3 Baths, sleeps 12 -  the pool is open & a few openings for Summer 2024 !, holiday rental in Great Barrington

5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !

Holiday Rental House
1.7 miles from Housatonic River Walk
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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
1.8 miles from Housatonic River Walk
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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River Cottage: Riverfront Home, Walkable Community, holiday rental in Great Barrington
River Cottage: Riverfront Home, Walkable Community, holiday rental in Great Barrington
River Cottage: Riverfront Home, Walkable Community, holiday rental in Great Barrington

River Cottage: Riverfront Home, Walkable Community

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
3.0 miles from Housatonic River Walk
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Pink Door Cottage - Bright, Cozy, Walk to Town, holiday rental in Great Barrington
The Pink Door Cottage - Bright, Cozy, Walk to Town, holiday rental in Great Barrington
The Pink Door Cottage - Bright, Cozy, Walk to Town, holiday rental in Great Barrington

The Pink Door Cottage - Bright, Cozy, Walk to Town

Holiday Rental House
1.4 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
4.5 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut, holiday rental in Great Barrington
A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut, holiday rental in Great Barrington
A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut, holiday rental in Great Barrington

A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut

Holiday Rental House
3.4 miles from Housatonic River Walk
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
3.4 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hang By The Pool or Walk To Town, holiday rental in Great Barrington
Hang By The Pool or Walk To Town, holiday rental in Great Barrington
Hang By The Pool or Walk To Town, holiday rental in Great Barrington

Hang By The Pool or Walk To Town

Holiday Rental House
0.6 miles from Housatonic River Walk
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
2.7 miles from Housatonic River Walk
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Great Barrington Lakeside Getaway w/ Kayak & Grill, holiday rental in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill, holiday rental in Great Barrington
Great Barrington Lakeside Getaway w/ Kayak & Grill, holiday rental in Great Barrington

Great Barrington Lakeside Getaway w/ Kayak & Grill

Holiday Rental House
3.7 miles from Housatonic River Walk
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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
4.1 miles from Housatonic River Walk
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
2.5 miles from Housatonic River Walk
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
5.2 miles from Housatonic River Walk
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Magical Country Retreat in the Berkshires, holiday rental in Great Barrington
Magical Country Retreat in the Berkshires, holiday rental in Great Barrington
Magical Country Retreat in the Berkshires, holiday rental in Great Barrington

Magical Country Retreat in the Berkshires

Holiday Rental House
9 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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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
2.1 miles from Housatonic River Walk
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ranch on 5+ acres & 0.7 mi to GB Main St.  Sleeps 10 + Wi-Fi + HOT TUB, holiday rental in Great Barrington
Ranch on 5+ acres & 0.7 mi to GB Main St.  Sleeps 10 + Wi-Fi + HOT TUB, holiday rental in Great Barrington
Ranch on 5+ acres & 0.7 mi to GB Main St.  Sleeps 10 + Wi-Fi + HOT TUB, holiday rental in Great Barrington

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

Holiday Rental House
0.7 miles from Housatonic River Walk
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Idyllic Retreat; Hot Tub/Sauna by Evergreen Home, holiday rental in Great Barrington
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home, holiday rental in Great Barrington
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home, holiday rental in Great Barrington

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Holiday Rental House
2.5 miles from Housatonic River Walk
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing  2-bedroom apartment sunny and quiet in Great Barrington, holiday rental in Great Barrington
Amazing  2-bedroom apartment sunny and quiet in Great Barrington, holiday rental in Great Barrington
Amazing  2-bedroom apartment sunny and quiet in Great Barrington, holiday rental in Great Barrington

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Condo/Apartment
0.1 miles from Housatonic River Walk
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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