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Holiday Rentals in Great Barrington

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62 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 travellers have booked this property
Lakefront Berkshires Ski/Summer House, Great Views
4 bedrooms
2 bathrooms
Sleeps 10
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3 other travellers have booked this property
Gem of the Berkshires, walk to downtown & lake.
5 bedrooms
4 bathrooms
Sleeps 12
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1 other traveller has booked this property
Shaker Hill
5 bedrooms
4 bathrooms
Sleeps 10
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3 other travellers have booked this property
Cozy and clean in Gt Barrington- available for October
2 bedrooms
2 bathrooms
Sleeps 4
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Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 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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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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2 other travellers have booked this property
The Smith Farm Homestead
1 bedroom
1 bathroom
Sleeps 2
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17 other travellers 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 travellers have booked this property
RiverSong Suite In The Berkshires
1 bedroom
1 bathroom
Sleeps 2
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31 other travellers have booked this property
Beautifully decorated & immaculate log chalet
3 bedrooms
2 bathrooms
Sleeps 6
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37 other travellers have booked this property
Family-friendly Cottage Near Lake, Tanglewood
3 bedrooms
2 bathrooms
Sleeps 7
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12 other travellers have booked this property
Tanglewood / Berkshires - 2 Bed 2 Bath Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travellers have booked this property
Charming Farmhouse on Magical 4 Acre Estate
4 bedrooms
3 bathrooms
Sleeps 8
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4 other travellers have booked this property
Romantic Berkshire Cottage on Storybook Estate
1 bedroom
1 bathroom
Sleeps 2
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6 other travellers have booked this property
Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
1 bedroom
1 bathroom
Sleeps 4
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1 other traveller has booked this property
Cozy & Modern Home -mins from Tanglewood & Kripalu
2 bedrooms
1 bathroom
Sleeps 6
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6 other travellers 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 travellers have booked this property
Mountain Views Atop Blueberry Hill on 40 Acres
3 bedrooms
3 bathrooms
Sleeps 6
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12 other travellers 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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Beautiful Cottage at the foot of the Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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Total Privacy! Tanglewood Retreat With Berkshire Views!
5 bedrooms
5 bathrooms
Sleeps 14
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1 other traveller has booked this property
Overnight at Althouse -Higgins
2 bedrooms
1 bathroom
Sleeps 4
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5 other travellers have booked this property
Comfortable Farmhouse in the Berkshires
5 bedrooms
3 bathrooms
Sleeps 12
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10 other travellers have booked this property
Lake House
5 bedrooms
6 bathrooms
Sleeps 9
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The perfect Southern Berkshire winter vacation esc
4 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Lakefront Berkshire Rental
5 bedrooms
2 bathrooms
Sleeps 6
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Newly Renovated Colonial on the River! Sleeps 5-6
3 bedrooms
2 bathrooms
Sleeps 5
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3BD Newly Rennovated Contempoary Near Stockbridge
3 bedrooms
3 bathrooms
Sleeps 6
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2 other travellers have booked this property
Restored 1886 Eyebrow Colonial
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travellers have booked this property
Tranquil 3BR Stockbridge House w/Private Deck
3 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
Iris Room
1 bedroom
1 bathroom
Sleeps 2
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1 other traveller has booked this property
Horse Room
1 bedroom
1 bathroom
Sleeps 3
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3BR Lee House w/ Easy Access to Main Street!
3 bedrooms
2 bathrooms
Sleeps 10
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Waterfront Cottage - 10 Mins to Great Barrington!
2 bedrooms
1 bathroom
Sleeps 4
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8 other travellers have booked this property
Beauty in the Berkshires
6 bedrooms
5 bathrooms
Sleeps 14
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Designer Loft Style Residence
3 bedrooms
3 bathrooms
Sleeps 6
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1 other traveller has booked this property
Spacious Lakeside Berkshire Home
4 bedrooms
5 bathrooms
Sleeps 10
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1 other traveller has booked this property
Beautifully Renovated Berkshires Farmhouse
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Stockbridge Home - Walk To Golf Course!
2 bedrooms
2 bathrooms
Sleeps 6
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Cozy Modern Condo for the Berkshires
2 bedrooms
1 bathroom
Sleeps 6
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1 other traveller has booked this property
One of the Finest Homes and Best location in the Berkshires
4 bedrooms
3 bathrooms
Sleeps 10
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RIVERSONG 'PENTHOUSE'
1 bedroom
1 bathroom
Sleeps 2
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1 other traveller has booked this property
Charming Private Guest Suite in Historic Village in the Berkshires
0 bedrooms
1 bathroom
Sleeps 2
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