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Great Barrington Holiday Rentals

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21 rentals in Great Barrington.
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Berkshires: Romantic Cottage with spectacular view, holiday rental in Great Barrington

Berkshires: Romantic Cottage with spectacular view

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful 1920's Colonial 20 Minutes from Tanglewood, holiday rental in Great Barrington

Beautiful 1920's Colonial 20 Minutes from Tanglewood

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, holiday rental in Great Barrington

The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants, holiday rental in Great Barrington

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Renovated Victorian, holiday rental in Great Barrington

Stunning Renovated Victorian

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Lake Community - Near Town, Attractions, holiday rental in Great Barrington

Lake Community - Near Town, Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE, holiday rental in Great Barrington

NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gem of the Berkshires, walk to downtown & lake., holiday rental in Great Barrington

Gem of the Berkshires, walk to downtown & lake.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington

Barn Apartment in Gorgeous Stonybrook Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Upscale Country Cottage, holiday rental in Great Barrington

Upscale Country Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington, holiday rental in Great Barrington

Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern Victorian on the Hill, holiday rental in Great Barrington

Modern Victorian on the Hill

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Berkshires Ski/Summer House, Great Views, holiday rental in Great Barrington

Lakefront Berkshires Ski/Summer House, Great Views

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Rustic modern house in Great Barrington near town, lake, Tanglewood and ski!, holiday rental in Great Barrington

Rustic modern house in Great Barrington near town, lake, Tanglewood and ski!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing, holiday rental in Great Barrington

Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing

0 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Eco-friendly cozy home in Gt. Barrington, holiday rental in Great Barrington

Eco-friendly cozy home in Gt. Barrington

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Home Overlooking Stevens Lake, holiday rental in Great Barrington

Private Home Overlooking Stevens Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort, holiday rental in Great Barrington

NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Impeccable House Minutes from Downtown Great Barrington, holiday rental in Great Barrington

Impeccable House Minutes from Downtown Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!, holiday rental in Great Barrington

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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