Berkshire County Vacation Rentals - HolidayHomes base64Hash Berkshire County Vacation Rentals - HolidayHomes

Berkshire County Vacation Rentals

Browse 2,258 available vacation homes and compared across 12 trusted partners

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Top-Rated Vacation rentals in Berkshire County

Book the highest-rated Berkshire County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Richmond
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
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Cabin New Marlborough
Waterfront Cottage 10 Min From Great Barrington
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House Hinsdale
Vacation home with BBQ & yard | Nature view
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Cabin Monterey
Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
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House Hinsdale
Vacation home with barbecue, yard & patio | Nature view
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House Lee
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks
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House Lenox
Vacation home with private pool & barbeque
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House Alford
Beautiful Berkshire Farm House on 160 Acres
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Cabin New Marlborough
Child-friendly charming cottage with barbeque & terrace | Pet-friendly
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Cabin Sandisfield
Come to the Berkshires for outdoor enthusiast, or a relaxing couple retreat
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House Stockbridge
Secluded + Modern | Enclosed Patio, Forest Views | Woodland Zen by AvantStay
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House Hinsdale
Family-oriented house with jacuzzi, terrace & garden | Suitable for remote work
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House Sandisfield
Vacation home with yard, barbecue & terrace | Nature view
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House Becket
House with garden, private pool & jacuzzi | Suitable for remote work
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Condo Lanesborough
Family-friendly condo with terrace, heated pool & sauna | Mountain view | Suitable for remote work | Dogs allowed
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Top 15 most Recommended Vacation Rentals in Berkshire County

Discover your ideal Berkshire County vacation rental with real-time comparisons of 2,258 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Williamstown
House ∙ 10 guests ∙ 3 bedrooms

Family-oriented beautiful vacation home with yard, barbeque & terrace | Good for workation | Pets allowed

Williamstown, Berkshire County, Massachusetts, United States
Spacious house rental in Williamstown accommodates 10 guests and features a family-friendly yard for outdoor fun.
from $760
per night
(32)
View deal
House Egremont
House ∙ 10 guests ∙ 5 bedrooms

Fully equipped spacious house with grill, patio & yard | Perfect for remote work | Pets are welcome

Egremont, Berkshire County, Massachusetts, United States
This house rental in Egremont accommodates 10 guests and features a private pool for a relaxing getaway.
from $1,400
per night
(12)
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House Stockbridge
House ∙ 24 guests ∙ 12 bedrooms

House with barbeque, terrace & garden

Stockbridge, Berkshire County, Massachusetts, United States
This spacious house rental in Stockbridge accommodates 24 guests and features a family-friendly kitchen perfect for gatherings.
from $716
per night
(70)
View deal
House Becket
House ∙ 7 guests ∙ 2 bedrooms

Fully equipped spacious house with grill & garden | Pet-friendly

Becket, Berkshire County, Massachusetts, United States
This house rental in Becket accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $199
per night
(31)
View deal
House Sherwood Forest
House ∙ 6 guests ∙ 2 bedrooms

Family-oriented beautiful house with barbecue, garden & terrace | Nature view | Pet-friendly

Sherwood Forest, Becket, Berkshire County
Charming house rental in Sherwood Forest accommodates 6 guests and features a family-friendly kitchen and a spacious yard.
from $182
per night
(284)
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House Great Barrington
House ∙ 12 guests ∙ 5 bedrooms

Family-friendly vacation home with patio, grill & yard | Nature view | Suitable for remote work

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 12 guests and features a private pool for a relaxing getaway.
from $465
per night
(159)
View deal
Cabin Hinsdale
Cabin ∙ 4 guests ∙ 2 bedrooms

Children-friendly spacious cabin with garden, grill & patio | Lake view

Hinsdale, Berkshire County, Massachusetts, United States
This cozy cabin in Hinsdale accommodates 4 guests and features a charming fireplace for a warm and inviting atmosphere.
from $197
per night
(69)
View deal
House Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly vacation home with yard, private pool & BBQ | Perfect for remote work | Dogs allowed

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $832
per night
(23)
View deal
House Otis
House ∙ 8 guests ∙ 2 bedrooms

Family-oriented vacation home with patio, yard & barbeque | Lake view | Suitable for remote work

Otis, Berkshire County, Massachusetts, United States
This house rental in Otis accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $273
per night
(73)
View deal

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