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Great Barrington Holiday Apartments

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41 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, 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
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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!, holiday rental in Great Barrington
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!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Location Location! Comfort and Privacy So Close to Downtown, holiday rental in Great Barrington
Location Location! Comfort and Privacy So Close to Downtown, holiday rental in Great Barrington
Location Location! Comfort and Privacy So Close to Downtown, holiday rental in Great Barrington

Location Location! Comfort and Privacy So Close to Downtown

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Barrington apartment, Short walk to downtown, holiday rental in Great Barrington
Great Barrington apartment, Short walk to downtown, holiday rental in Great Barrington
Great Barrington apartment, Short walk to downtown, holiday rental in Great Barrington

Great Barrington apartment, Short walk to downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Berkshire Farm House on 160+ Acres, holiday rental in Great Barrington
Beautiful Berkshire Farm House on 160+ Acres, holiday rental in Great Barrington
Beautiful Berkshire Farm House on 160+ Acres, holiday rental in Great Barrington

Beautiful Berkshire Farm House on 160+ Acres

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 16
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
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
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
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, holiday rental in Great Barrington
NEW SECLUDED 3 BEDROOM COUNTRY CASTLE, holiday rental in Great Barrington

NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14, holiday rental in Great Barrington
CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14, holiday rental in Great Barrington
CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14, holiday rental in Great Barrington

CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Charming Housatonic Village Cape, holiday rental in Great Barrington
Charming Housatonic Village Cape, holiday rental in Great Barrington
Charming Housatonic Village Cape, holiday rental in Great Barrington

Charming Housatonic Village Cape

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Monthly Discount  for Ski Season Rental at Lakefront House in Great Barrington, holiday rental in Great Barrington
Monthly Discount  for Ski Season Rental at Lakefront House in Great Barrington, holiday rental in Great Barrington
Monthly Discount  for Ski Season Rental at Lakefront House in Great Barrington, holiday rental in Great Barrington

Monthly Discount for Ski Season Rental at Lakefront House in Great Barrington

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!, holiday rental in Great Barrington
HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!, holiday rental in Great Barrington
HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!, holiday rental in Great Barrington

HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Deluxe Home w/ Pool on The Hill, holiday rental in Great Barrington
Deluxe Home w/ Pool on The Hill, holiday rental in Great Barrington
Deluxe Home w/ Pool on The Hill, holiday rental in Great Barrington

Deluxe Home w/ Pool on The Hill

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington
Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington
Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Great Barrington

Barn Apartment in Gorgeous Stonybrook Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!, holiday rental in Great Barrington
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!, holiday rental in Great Barrington
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!, holiday rental in Great Barrington

Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Serene Great Barrington Cottage w/ Fire Pit!, holiday rental in Great Barrington
NEW! Serene Great Barrington Cottage w/ Fire Pit!, holiday rental in Great Barrington
NEW! Serene Great Barrington Cottage w/ Fire Pit!, holiday rental in Great Barrington

NEW! Serene Great Barrington Cottage w/ Fire Pit!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Modern Victorian on the Hill, holiday rental in Great Barrington
Modern Victorian on the Hill, holiday rental in Great Barrington
Modern Victorian on the Hill, holiday rental in Great Barrington

Modern Victorian on the Hill

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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
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New to Market Renovated Home, 5 min walk to town, holiday rental in Great Barrington
New to Market Renovated Home, 5 min walk to town, holiday rental in Great Barrington
New to Market Renovated Home, 5 min walk to town, holiday rental in Great Barrington

New to Market Renovated Home, 5 min walk to town

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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., holiday rental in Great Barrington
Gem of the Berkshires, walk to downtown & lake., holiday rental in Great Barrington

Gem of the Berkshires, walk to downtown & lake.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Upscale Country Cottage, holiday rental in Great Barrington
Upscale Country Cottage, holiday rental in Great Barrington
Upscale Country Cottage, holiday rental in Great Barrington

Upscale Country Cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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, holiday rental in Great Barrington
Lakefront Berkshires Ski/Summer House, Great Views, holiday rental in Great Barrington

Lakefront Berkshires Ski/Summer House, Great Views

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A Four Seasons Woodland Lodge, holiday rental in Great Barrington
A Four Seasons Woodland Lodge, holiday rental in Great Barrington
A Four Seasons Woodland Lodge, holiday rental in Great Barrington

A Four Seasons Woodland Lodge

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr, holiday rental in Great Barrington
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr, holiday rental in Great Barrington
NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr, holiday rental in Great Barrington

NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A great escape; secluded but close to all - contemporary home, mountain views, holiday rental in Great Barrington
A great escape; secluded but close to all - contemporary home, mountain views, holiday rental in Great Barrington
A great escape; secluded but close to all - contemporary home, mountain views, holiday rental in Great Barrington

A great escape; secluded but close to all - contemporary home, mountain views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
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 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town., holiday rental in Great Barrington
Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town., holiday rental in Great Barrington
Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town., holiday rental in Great Barrington

Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic Berkshire Cottage in Sun-Drenched Meadow, holiday rental in Great Barrington
Classic Berkshire Cottage in Sun-Drenched Meadow, holiday rental in Great Barrington
Classic Berkshire Cottage in Sun-Drenched Meadow, holiday rental in Great Barrington

Classic Berkshire Cottage in Sun-Drenched Meadow

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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, holiday rental in Great Barrington
Eco-friendly cozy home in Gt. Barrington, holiday rental in Great Barrington

Eco-friendly cozy home in Gt. Barrington

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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 10
Match: Sleeps
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Renovated family friendly house close to everything and endless views, holiday rental in Great Barrington
Renovated family friendly house close to everything and endless views, holiday rental in Great Barrington
Renovated family friendly house close to everything and endless views, holiday rental in Great Barrington

Renovated family friendly house close to everything and endless views

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Luxurious modern estate w/ heated pool, hot tub, and lakefront!, holiday rental in Great Barrington
Luxurious modern estate w/ heated pool, hot tub, and lakefront!, holiday rental in Great Barrington
Luxurious modern estate w/ heated pool, hot tub, and lakefront!, holiday rental in Great Barrington

Luxurious modern estate w/ heated pool, hot tub, and lakefront!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Farmhouse from a magazine, holiday rental in Great Barrington
Farmhouse from a magazine, holiday rental in Great Barrington
Farmhouse from a magazine, holiday rental in Great Barrington

Farmhouse from a magazine

Holiday Rental House
3 bedrooms
4 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, holiday rental in Great Barrington
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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!, holiday rental in Great Barrington
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!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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