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

Berkshire County Vacation Rentals

Browse 2,344 available vacation homes and compared across 13 trusted partners

Anytime
Guests
Anytime
Guests

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

Top 15 most Recommended Vacation Rentals in Berkshire County

Discover your ideal Berkshire County vacation rental with real-time comparisons of 2,344 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Great Barrington
House ∙ 10 guests ∙ 4 bedrooms

185 m² House

Great Barrington, Berkshire County, Massachusetts, United States
Spacious house rental in Great Barrington for 10 guests featuring a cozy fireplace and stunning mountain views.
from $317
per night
(61)
View deal
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 $427
per night
(78)
View deal
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 $385
per night
(16)
View deal
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 $349
per night
(2)
View deal
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 $195
per night
(208)
View deal
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 $341
per night
(5)
View deal
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 $235
per night
View deal
House Becket
House ∙ 5 guests ∙ 2 bedrooms

102 m² House

Becket, Berkshire County, Massachusetts, United States
Charming house rental in Becket for 6 with a cozy fireplace and a spacious yard perfect for family gatherings.
from $218
per night
(26)
View deal
Cabin New Marlborough
Cabin ∙ 2 guests ∙ 1 bedroom

69 m² Cabin

New Marlborough, Berkshire County, Massachusetts, United States
A cozy cabin in New Marlborough for 2 guests featuring a beautiful lakeview and a fully equipped kitchen.
from $226
per night
(143)
View deal

More travel options

image-tag