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Great Barrington Vacation Rentals

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42 rentals in Great Barrington.
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Berkshires: Romantic Cottage with spectacular view

Rental Home
1 bedroom
1 bathroom
Sleeps 3
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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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
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Location Location! Comfort and Privacy So Close to Downtown

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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2 bedroom Riverhouse in the Heart of the Berkshires

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Barrington apartment, Short walk to downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Stunning Renovated Victorian

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Berkshire Farm House on 160+ Acres

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Minutes from downtown Great Barrington, Convenient location

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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COZY LOG HOME* fireplace, skiing,fall foliage Hiking, Berkshires*

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Lake Community - Near Town, Attractions

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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CHIC UPDATED DOWNTOWN Great Barrington, Sleeps 14

Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Charming Housatonic Village Cape

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Monthly Discount for Ski Season Rental at Lakefront House in Great Barrington

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!

Rental Home
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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Romantic Berkshires Cottage - Stunning Views, Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Deluxe Home w/ Pool on The Hill

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Barn Apartment in Gorgeous Stonybrook Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Minutes from Butternut Ski, Tanglewood and downtown Great Barrington

Rental Home
7 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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NEW! Serene Great Barrington Cottage w/ Fire Pit!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Idyllic Berkshire Get Away: Balance of relaxation and convenience

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New to Market Renovated Home, 5 min walk to town

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Victorian on the Hill

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Gem of the Berkshires, walk to downtown & lake.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Upscale Country Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Berkshires Ski/Summer House, Great Views

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A Four Seasons Woodland Lodge

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A great escape; secluded but close to all - contemporary home, mountain views

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful house on 'The Hill' just minutes from Lake Mansfield and Town.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Classic Berkshire Cottage in Sun-Drenched Meadow

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Eco-friendly cozy home in Gt. Barrington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated house on the Hill. Walk everywhere!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Renovated family friendly house close to everything and endless views

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious modern estate w/ heated pool, hot tub, and lakefront!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Farmhouse from a magazine

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Cozy Great Barrington Home 1 Mi to Ski Resort

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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