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Berkshires House Rentals

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208 rentals in Berkshires.
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Certificate of Excellence
Berkshires Waterfront Lakehouse Sanctuary
8 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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14 other travellers have booked this property
Lakefront Berkshires Ski/Summer House, Great Views
4 reviews
4 bedrooms
2 bathrooms
Sleeps 10
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3 other travellers have booked this property
Great Vacation House in the Berkshires by Richmond Pond
4 reviews
2 bedrooms
1 bathroom
Sleeps 6
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6 other travellers have booked this property
Escape to the Berkshires!
4 reviews
4 bedrooms
3 bathrooms
Sleeps 8
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6 other travellers have booked this property
Quiet Comfortable Cabin 5 Min. Walk to Lake
13 reviews
2 bedrooms
1 bathroom
Sleeps 4
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21 other travellers have booked this property
Restored 1886 Eyebrow Colonial
1 review
2 bedrooms
2 bathrooms
Sleeps 6
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2 other travellers have booked this property
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
7 reviews
3 bedrooms
3 bathrooms
Sleeps 8
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14 other travellers have booked this property
Berkshire Farmhouse Vacation
42 reviews
5 bedrooms
2 bathrooms
Sleeps 15
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18 other travellers have booked this property
Gem of the Berkshires, walk to downtown & lake.
4 reviews
5 bedrooms
4 bathrooms
Sleeps 12
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1 other traveller has booked this property
Retreat in the Woods
8 reviews
2 bedrooms
1 bathroom
Sleeps 4
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25 other travellers have booked this property
2200sf Country House on 16 Acres-2 Miles to Jiminy
3 reviews
4 bedrooms
2 bathrooms
Sleeps 9
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3 other travellers have booked this property
Shaker Hill
2 reviews
5 bedrooms
4 bathrooms
Sleeps 10
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3 other travellers have booked this property
Spacious Lakeside Berkshire Home
4 bedrooms
5 bathrooms
Sleeps 10
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1 other traveller has booked this property
Designer Loft Style Residence
3 bedrooms
3 bathrooms
Sleeps 6
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1 other traveller has booked this property
Lake House
5 reviews
5 bedrooms
6 bathrooms
Sleeps 9
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Whitman Woods - A Berkshire Vacation
1 review
4 bedrooms
2 bathrooms
Sleeps 8
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2 other travellers have booked this property
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
0 bedrooms
1 bathroom
Sleeps 4
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New England Style 2BR Suite at Vacation Village in the Berkshire
2 bedrooms
1 bathroom
Sleeps 6
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2BR Suite w Pools at Vacation Village in the Berkshires
2 bedrooms
1 bathroom
Sleeps 6
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Big Beautiful 7 bedroom 3 bath hot tub pool table
7 bedrooms
3 bathrooms
Sleeps 18
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1 other traveller has booked this property
Heart of Lenox
2 reviews
2 bedrooms
2 bathrooms
Sleeps 4
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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
Spacious wooded home
4 bedrooms
6 bathrooms
Sleeps 12
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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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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
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
Tranquil 3BR Stockbridge House w/Private Deck
2 reviews
3 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
Newly Renovated Colonial on the River! Sleeps 5-6
1 review
3 bedrooms
2 bathrooms
Sleeps 5
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One of the Finest Homes and Best location in the Berkshires
4 bedrooms
3 bathrooms
Sleeps 10
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Country Victorian Serenity in the Berkshires
4 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Lakefront Berkshire Rental
5 bedrooms
2 bathrooms
Sleeps 6
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3BR Lee House w/ Easy Access to Main Street!
3 bedrooms
2 bathrooms
Sleeps 10
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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
Vacation Home on 10 Acres with Pool and Spa
3 bedrooms
2 bathrooms
Sleeps 6
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New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)
3 bedrooms
3 bathrooms
Sleeps 6
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Golden Triangle in the Berkshires
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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4 other travellers have booked this property
Cozy and clean in Gt Barrington- available for October
1 review
2 bedrooms
2 bathrooms
Sleeps 4
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Serene Lakefront Cottage
13 reviews
2 bedrooms
2 bathrooms
Sleeps 6
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Stunning Home! 120 Acres! Amazing!
9 bedrooms
8 bathrooms
Sleeps 16
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NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!
3 bedrooms
3 bathrooms
Sleeps 6
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1 other traveller has booked this property
Berkshires on the Pond
2 bedrooms
2 bathrooms
Sleeps 2
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Berkshire Getaway Home with Lake Access
1 review
4 bedrooms
2 bathrooms
Sleeps 10
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Private Berkshire Estate w/Pool & Tennis Court
4 bedrooms
4 bathrooms
Sleeps 12
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Deluxe New Home, 2 Master Suites, Tanglewood Area
5 bedrooms
5 bathrooms
Sleeps 12
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Zen Cottage in the Woods
3 bedrooms
1 bathroom
Sleeps 6
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Ranch at Fox Hollow - Laurel Lake , 4BR's, 4.5 Baths
4 bedrooms
5 bathrooms
Sleeps 11
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Fabulous Post & Beam Berkshire Rental
0 bedrooms
2 bathrooms
Sleeps 7
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Restored 1881 Farm House
2 bedrooms
2 bathrooms
Sleeps 4
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Luxury Fox Hollow Estate Home on Laurel Lake, Hot Tub, Dock with Kayak, Canoe++
5 bedrooms
3 bathrooms
Sleeps 14
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End of Winter Sale: SAVE 20% March 1 - May 1!! Skiers' Delight! Less than 4 mile
3 bedrooms
2 bathrooms
Sleeps 6
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