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Holiday Rentals in Berkshires

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91 rentals in Berkshires.
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Berkshires Spacious Comfortable Charming Farmhouse
3 bedrooms
2 bathrooms
Sleeps 8
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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
Gartner House, a charming home in Lenox
4 bedrooms
1 bathroom
Sleeps 7
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40 other travellers have booked this property
Unique People & Pet-Welcoming Country Haven
1 bedroom
1 bathroom
Sleeps 4
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24 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
Quiet Comfortable Cabin 5 Min. Walk to Lake
2 bedrooms
1 bathroom
Sleeps 4
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21 other travellers have booked this property
Shaker Hill
5 bedrooms
4 bathrooms
Sleeps 10
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3 other travellers have booked this property
'Fall' in love with the Berkshire or 'Winter in !!!
3 bedrooms
3 bathrooms
Sleeps 8
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14 other travellers have booked this property
Golden Triangle in the Berkshires
2 bedrooms
2 bathrooms
Sleeps 4
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4 other travellers have booked this property
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Family-friendly Cottage Near Lake, Tanglewood
3 bedrooms
2 bathrooms
Sleeps 7
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12 other travellers have booked this property
Eco-friendly cozy home in Gt. Barrington
3 bedrooms
2 bathrooms
Sleeps 4
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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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3 other travellers have 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
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE
5 bedrooms
3 bathrooms
Sleeps 14
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1 other traveller has booked this property
Escape to the Berkshires!
4 bedrooms
3 bathrooms
Sleeps 8
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6 other travellers have booked this property
Apartment walking distance to Mass MoCa!!
2 bedrooms
1 bathroom
Sleeps 10
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9 other travellers have booked this property
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
3 bedrooms
2 bathrooms
Sleeps 6
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11 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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Retreat in the Woods
2 bedrooms
1 bathroom
Sleeps 4
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25 other travellers have booked this property
Fabulous Post & Beam Berkshire Rental
0 bedrooms
2 bathrooms
Sleeps 7
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Jiminy Peak Ski Resort-Country Village's Best Unit
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travellers have booked this property
House On Main Street
4 bedrooms
5 bathrooms
Sleeps 16
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ROOM walking distance to Mass MoCa
1 bedroom
2 bathrooms
Sleeps 8
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4 other travellers have booked this property
3 BR apartment, walking distance to Mass MoCa
3 bedrooms
1 bathroom
Sleeps 15
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3 other travellers have booked this property
Lake House
5 bedrooms
6 bathrooms
Sleeps 9
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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES
6 bedrooms
5 bathrooms
Sleeps 14
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1 other traveller has booked this property
Beautiful Lakefront Berkshire Rental
5 bedrooms
2 bathrooms
Sleeps 6
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Christmas in The Berkshires
1 bedroom
2 bathrooms
Sleeps 4
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1 other traveller has booked this property
Newly Renovated Colonial on the River! Sleeps 5-6
3 bedrooms
2 bathrooms
Sleeps 5
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1 other traveller has booked this property
Enjoy horses and the largest recreational lake in Massachusetts
1 bedroom
1 bathroom
Sleeps 4
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1 other traveller has booked this property
3BD Newly Rennovated Contempoary Near Stockbridge
3 bedrooms
3 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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Thanksgiving week lux condo/4 Berkshires
2 bedrooms
1 bathroom
Sleeps 4
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3BR Lee House w/ Easy Access to Main Street!
3 bedrooms
2 bathrooms
Sleeps 10
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Fox Hollow Laurel Lake Ranch
4 bedrooms
5 bathrooms
Sleeps 11
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3 other travellers have booked this property
Waterfront Cottage - 10 Mins to Great Barrington!
2 bedrooms
1 bathroom
Sleeps 4
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7 other travellers have booked this property
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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Heart of Lenox
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Modern Condo for the Berkshires
2 bedrooms
1 bathroom
Sleeps 6
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2 other travellers have booked this property
One of the Finest Homes and Best location in the Berkshires
4 bedrooms
3 bathrooms
Sleeps 10
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