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Great Barrington Vacation Rentals

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$1,000+
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82 rentals in Great Barrington.
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Berkshires: Romantic Cottage with spectacular view
1 bedroom
1 bathroom
Sleeps 3
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17 other travelers have booked this property
Lakefront Berkshires Ski/Summer House, Great Views
4 bedrooms
2 bathrooms
Sleeps 10
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3 other travelers have booked this property
Gem of the Berkshires, walk to downtown & lake.
5 bedrooms
4 bathrooms
Sleeps 12
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1 other traveler has booked this property
Shaker Hill
5 bedrooms
4 bathrooms
Sleeps 10
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3 other travelers have booked this property
Cozy and clean in Gt Barrington- available for October
2 bedrooms
2 bathrooms
Sleeps 4
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A Beautiful Cabin In The Heart Of The Berkshires
3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Berkshire Retreat
5 bedrooms
5 bathrooms
Sleeps 12
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Great Barrington Retreat ! Booking for the Fall Now!
3 bedrooms
3 bathrooms
Sleeps 7
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Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire Theater
3 bedrooms
2 bathrooms
Sleeps 8
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Family Home With Big Yard On The Hill, Short Walk To Downtown And Lake Mansfield
4 bedrooms
2 bathrooms
Sleeps 8
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Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!
5 bedrooms
3 bathrooms
Sleeps 10
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Minutes from downtown Great Barrington, Convenient location
4 bedrooms
3 bathrooms
Sleeps 8
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Lake Community - Near Town, Attractions - 2020 MA Residents Only
2 bedrooms
1 bathroom
Sleeps 6
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HOT TUB, FIREPLACE, BEAUTIFUL, COMFORTABLE, WALK TO RESTAURANTS, WEEKEND RATES!
5 bedrooms
3 bathrooms
Sleeps 10
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Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
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Charming Housatonic Village Cape
4 bedrooms
2 bathrooms
Sleeps 10
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Stunning Renovated Victorian
5 bedrooms
5 bathrooms
Sleeps 12
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Great Barrington - The Cottage at Windflower Inn - Low Price - Close to Skiing
0 bedrooms
3 bathrooms
Sleeps 9
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Romantic Berkshires Cottage - Stunning Views, Pool
1 bedroom
1 bathroom
Sleeps 3
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Barn Apartment in Gorgeous Stonybrook Farm
1 bedroom
1 bathroom
Sleeps 2
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Charming, Newly Renovated Home Close to All Berkshire Attractions
4 bedrooms
3 bathrooms
Sleeps 10
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Rustic modern house in Great Barrington near town, lake, Tanglewood and ski!
4 bedrooms
3 bathrooms
Sleeps 8
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Open Field House with a View! Dog friendly
3 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Berkshire Farm House on 160+ Acres
7 bedrooms
5 bathrooms
Sleeps 16
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Berkshire Mountain Cottage: in the Heart of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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Luxurious Modern on 4 acres - sleeps 8-12
4 bedrooms
5 bathrooms
Sleeps 12
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1 Mile from Butternut! Close to Lakes, Appalachian Trail, Restaurants, Theatre.
5 bedrooms
3 bathrooms
Sleeps 12
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Sold out for the summer. Booking for fall, winter & all '21! Room for 12!
5 bedrooms
3 bathrooms
Sleeps 12
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Private Home Overlooking Stevens Lake
3 bedrooms
2 bathrooms
Sleeps 6
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NEW LISTING SPECIAL! SAVE 10%! Impeccable House Minutes from Downtown Great Barr
4 bedrooms
4 bathrooms
Sleeps 8
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Turning Point - Family Retreat & Group Getaway
7 bedrooms
8 bathrooms
Sleeps 15
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A Four Seasons Woodland Lodge
5 bedrooms
3 bathrooms
Sleeps 8
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The Hemlock House - 1.5 miles to GB and 4 miles to Ski Butternutt
3 bedrooms
2 bathrooms
Sleeps 8
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2 bedroom Riverhouse in the Heart of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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Berkshires Spacious Comfortable Charming Farmhouse
3 bedrooms
2 bathrooms
Sleeps 8
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Hillhouse Log Cabin
3 bedrooms
2 bathrooms
Sleeps 13
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3 other travelers have booked this property
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
3 bedrooms
3 bathrooms
Sleeps 8
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14 other travelers have booked this property
RiverSong Suite In The Berkshires
1 bedroom
1 bathroom
Sleeps 2
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31 other travelers have booked this property
Beautifully decorated & immaculate log chalet
3 bedrooms
2 bathrooms
Sleeps 6
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37 other travelers have booked this property
Family-friendly Cottage Near Lake, Tanglewood
3 bedrooms
2 bathrooms
Sleeps 7
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12 other travelers have booked this property
Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travelers have booked this property
Charming Farmhouse on Magical 4 Acre Estate
4 bedrooms
3 bathrooms
Sleeps 8
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4 other travelers have booked this property
Romantic Berkshire Cottage on Storybook Estate
1 bedroom
1 bathroom
Sleeps 2
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6 other travelers have booked this property
Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
1 bedroom
1 bathroom
Sleeps 4
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2 other travelers have booked this property
Cozy & Modern Home -mins from Tanglewood & Kripalu
2 bedrooms
1 bathroom
Sleeps 6
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6 other travelers have booked this property
Deluxe New Home, 2 Master Suites, Tanglewood Area
5 bedrooms
5 bathrooms
Sleeps 12
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Berkshire Farmhouse Vacation
5 bedrooms
2 bathrooms
Sleeps 15
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18 other travelers have booked this property
Mountain Views Atop Blueberry Hill on 40 Acres
3 bedrooms
3 bathrooms
Sleeps 6
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12 other travelers have booked this property
Vacation Home on 10 Acres with Pool and Spa
3 bedrooms
2 bathrooms
Sleeps 6
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Fabulous Post & Beam Berkshire Rental
0 bedrooms
2 bathrooms
Sleeps 7
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