The Berkshires Vacation Rentals - Wimdu base64Hash The Berkshires Vacation Rentals - Wimdu

The Berkshires Vacation Rentals

The Berkshires
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Pet-friendly rentals in The Berkshires

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

Cottage Monterey
$160 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.7
Excellent (66 ratings)
Monterey, Berkshire County, Massachusetts, United States
Pet-friendly
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House Stockbridge
$329 per night
House ∙ 8 guests ∙ 4 bedrooms
4.9
Outstanding (117 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
Pet-friendly
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Cottage New Fairfield
$91 per night
Cottage ∙ 4 guests ∙ 1 bedroom
4.6
Excellent (101 ratings)
New Fairfield, Fairfield County, Connecticut, United States
Pet-friendly
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Accommodation with Internet in The Berkshires

Choose your ideal rental with Internet and WiFi in The Berkshires

House Otis
$227 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (1 rating)
Otis, Berkshire County, Massachusetts, United States
Internet
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Cottage Lakeville
$531 per night
Cottage ∙ 18 guests ∙ 5 bedrooms
4.7
Excellent (87 ratings)
Lakeville, Salisbury, Connecticut, United States
Internet
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House Monterey
$473 per night
House ∙ 10 guests ∙ 5 bedrooms
4.7
Excellent (44 ratings)
Monterey, Berkshire County, Massachusetts, United States
Internet
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Vacation rentals with pool in The Berkshires

Discover best cabin and house rentals with pool in The Berkshires

House Hancock
$673 per night
House ∙ 14 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Hancock, Berkshire County, Massachusetts, United States
Pool
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House Ridgefield
$167 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (1 rating)
Ridgefield, Fairfield County, Connecticut, United States
Pool
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House Egremont
$696 per night
House ∙ 17 guests ∙ 7 bedrooms
5.0
Outstanding (6 ratings)
Egremont, Berkshire County, Massachusetts, United States
Pool
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Best vacation rental offers in The Berkshires

Cabin Becket
$113 per night
Cabin ∙ 5 guests ∙ 1 bedroom
4.9
Outstanding (206 ratings)
Becket, Berkshire County, Massachusetts, United States
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House Stockbridge
$359 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (18 ratings)
Stockbridge, Berkshire County, Massachusetts, United States
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House South Lee
$579 per night
House ∙ 8 guests ∙ 4 bedrooms
4.8
Outstanding (30 ratings)
South Lee, Lee, Massachusetts, United States
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Cottage Taconic
$177 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.8
Outstanding (213 ratings)
Taconic, Salisbury, Connecticut, United States
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House Hinsdale
$257 per night
House ∙ 8 guests ∙ 2 bedrooms
4.5
Excellent (67 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
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Cottage Otis
$181 per night
Cottage ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding (25 ratings)
Otis, Berkshire County, Massachusetts, United States
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House Pittsfield
$427 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (41 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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House Copake
$165 per night
House ∙ 9 guests ∙ 3 bedrooms
4.2
Very good (10 ratings)
Copake, Columbia County, New York, United States
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House Lee
$1,457 per night
House ∙ 20 guests ∙ 6 bedrooms
4.9
Outstanding (239 ratings)
Lee, Berkshire County, Massachusetts, United States
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House Stephentown
$126 per night
House ∙ 4 guests ∙ 2 bedrooms
Stephentown, Rensselaer County, New York, United States
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House New Ashford
$205 per night
House ∙ 6 guests ∙ 5 bedrooms
4.7
Excellent (64 ratings)
New Ashford, Berkshire County, Massachusetts, United States
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House Pittsfield
$649 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (92 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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House Lenox
$392 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (32 ratings)
Lenox, Berkshire County, Massachusetts, United States
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House Dalton
$267 per night
House ∙ 10 guests ∙ 5 bedrooms
4.9
Outstanding (45 ratings)
Dalton, Berkshire County, Massachusetts, United States
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House Morris
$279 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (3 ratings)
Morris, Litchfield County, Connecticut, United States
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House New Fairfield
$351 per night
House ∙ 9 guests ∙ 3 bedrooms
5.0
Outstanding (54 ratings)
New Fairfield, Fairfield County, Connecticut, United States
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House Sheffield
$267 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (186 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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House Great Barrington
$333 per night
House ∙ 10 guests ∙ 4 bedrooms
3.8
Good (50 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Cottage New Marlborough
$222 per night
Cottage ∙ 2 guests ∙ 1 bedroom
4.6
Excellent (42 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
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Cabin Sandisfield
$297 per night
Cabin ∙ 10 guests ∙ 4 bedrooms
4.9
Outstanding (37 ratings)
Sandisfield, Berkshire County, Massachusetts, United States
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Cottage Hinsdale
$272 per night
Cottage ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (27 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
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Cabin Otis
$231 per night
Cabin ∙ 7 guests ∙ 3 bedrooms
4.8
Outstanding (4 ratings)
Otis, Berkshire County, Massachusetts, United States
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House Sheffield
$256 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (14 ratings)
Sheffield, Berkshire County, Massachusetts, United States
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Farmhouse Charlemont
$332 per night
Farmhouse ∙ 8 guests ∙ 4 bedrooms
5.0
Outstanding (4 ratings)
Charlemont, Franklin County, Massachusetts, United States
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House West Stockbridge
$380 per night
House ∙ 8 guests ∙ 3 bedrooms
4.9
Outstanding (21 ratings)
West Stockbridge, Berkshire County, Massachusetts, United States
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House Copake
$443 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (29 ratings)
Copake, Columbia County, New York, United States
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House Lenox
$291 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (30 ratings)
Lenox, Berkshire County, Massachusetts, United States
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Cabin Southfield
$242 per night
Cabin ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding (37 ratings)
Southfield, New Marlborough, Massachusetts, United States
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House Lenox
$252 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (35 ratings)
Lenox, Berkshire County, Massachusetts, United States
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House Lenox
$295 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (82 ratings)
Lenox, Berkshire County, Massachusetts, United States
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House Brookfield
$91 per night
House ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding (10 ratings)
Brookfield, Fairfield County, Connecticut, United States
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House New Marlborough
$683 per night
House ∙ 8 guests ∙ 4 bedrooms
4.7
Excellent (24 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
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House New Fairfield
$398 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (25 ratings)
New Fairfield, Fairfield County, Connecticut, United States
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Cottage New Marlborough
$83 per night
Cottage ∙ 4 guests ∙ 1 bedroom
4.8
Outstanding (65 ratings)
New Marlborough, Berkshire County, Massachusetts, United States
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Apartment Winsted
$121 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding (2 ratings)
Winsted, Winchester, Connecticut, United States
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House Lanesborough
$544 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding (2 ratings)
Lanesborough, Berkshire County, Massachusetts, United States
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House Sherwood Forest
$402 per night
House ∙ 10 guests ∙ 6 bedrooms
5.0
Outstanding (91 ratings)
Sherwood Forest, Becket, Massachusetts, United States
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House Otis
$240 per night
House ∙ 7 guests ∙ 3 bedrooms
4.9
Outstanding (20 ratings)
Otis, Berkshire County, Massachusetts, United States
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House Hinsdale
$574 per night
House ∙ 6 guests ∙ 6 bedrooms
4.9
Outstanding (12 ratings)
Hinsdale, Berkshire County, Massachusetts, United States
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Price and Availability Index in The Berkshires

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Vacation Rental Price Information in The Berkshires

We analyzed data from the last 12 months and built the graph above to show you accommodation prices in The Berkshires. Vacation rental prices in The Berkshires are at their highest in August and reach on average $452 per night. In contrast, February and the period of 2/3 - 2/10 are the most affordable in the year, with vacation rental prices at $350 per night.

Rental availability information in The Berkshires

Here, you can see how busy The Berkshires will be at different times of year. The busiest time of year in The Berkshires is May. The week with the highest availability is in December (12/9 - 12/16) - 71% of the vacation rentals are still available.

And we love our apartments

Cabin
84 m² House
325 m² House
88 m² Cottage
102 m² House
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Beautiful regions abroad to consider for next trip

Beautiful regions near to consider for next trip

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