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

Berkshire County Vacation Rentals

Browse 2,342 available vacation homes and compared across 13 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 Otis
House with yard, grill & patio | Lake view
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House Sandisfield
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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House Great Barrington
5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!
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House Richmond
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
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House Lee
Spectacular setting on your own private lake close to it all!
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Cabin Monterey
Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
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House Stockbridge
Just a min from Downtown Stockbridge on 11 Acres
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House Stockbridge
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
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Apartment Hancock
Family-Friendly Hancock Home: Walk to Slopes!
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House Lee
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks
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House Stockbridge
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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House Lee
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
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House Monterey
Dock on Lake Garfield, 10 min to Butternut, Wifi, So Fun!
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House Monterey
Monterey Home w/ Hot Tub, Pool & Game Room!
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Cabin East Otis
East Otis Vacation Rental w/ Private Deck & BBQ!
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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 2,342 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Sandisfield
House ∙ 9 guests ∙ 4 bedrooms

184 m² House

Sandisfield, Berkshire County, Massachusetts, United States
This house rental in Sandisfield accommodates 9 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $287
per night
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House Hancock
House ∙ 15 guests ∙ 4 bedrooms

197 m² House

Hancock, Berkshire County, Massachusetts, United States
Spacious house rental in Hancock for 15 guests featuring a family-friendly kitchen and ample parking for a comfortable stay.
from $503
per night
(78)
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Cabin Otis
Cabin ∙ 6 guests ∙ 2 bedrooms

102 m² Cabin

Otis, Berkshire County, Massachusetts, United States
Cozy cabin in Otis accommodating 6 guests featuring a fireplace and a beautiful lakeview for a perfect retreat.
from $393
per night
(16)
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House New Marlborough
8 guests ∙ 4 bedrooms

House

New Marlborough, Berkshire County, Massachusetts, United States
This house rental in New Marlborough accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $361
per night
(2)
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House Peru
House ∙ 6 guests ∙ 3 bedrooms

153 m² House

Peru, Berkshire County, Massachusetts, United States
This house rental in Peru accommodates 6 guests and features a family-friendly kitchen with a beautiful mountain view.
from $199
per night
(208)
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House Egremont
House ∙ 8 guests ∙ 4 bedrooms

278 m² House

Egremont, Berkshire County, Massachusetts, United States
This house rental in Egremont accommodates 8 guests and features a kitchen for convenient meal preparation.
from $273
per night
(5)
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House Sandisfield
House ∙ 6 guests ∙ 4 bedrooms

251 m² House

Sandisfield, Berkshire County, Massachusetts, United States
Charming house rental in Sandisfield accommodates 6 guests and features a cozy fireplace for a perfect family getaway.
from $273
per night
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House Lee
House ∙ 14 guests ∙ 5 bedrooms

260 m² House

Lee, Berkshire County, Massachusetts, United States
This house rental in Lee accommodates 14 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $830
per night
(108)
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House Pittsfield
House ∙ 10 guests ∙ 3 bedrooms

167 m² House

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $383
per night
(95)
View deal

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