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

Berkshire County Vacation Rentals

Browse 2,301 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

We use AI to generate the short summary in each offer below, check full description before booking.
Cabin Sherwood Forest

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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House East Otis

House with yard, grill & patio | Lake view

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House Richmond

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

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House North Adams

Berkshire's Best~~On the Water~~Mt. Views, Museums, Paddling, Hiking, Relaxing

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House Pittsfield

Beautiful Waterfront home with deep water dock on Onota Lake. Huge covered deck.

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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 Lenox

Vacation home with private pool, hot tub & barbeque

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House Pittsfield

Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake

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Cabin Becket

Lakefront Cottage In The Berkshires In Western Massachusetts

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House Hancock

Vacation home with jacuzzi, pool & grill

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Cabin Sandisfield

Come to the Berkshires for outdoor enthusiast, or a relaxing couple retreat

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Chalet Monterey

Beautiful, Private Berkshires Retreat w Magic View! 5min to Lake Garfield Beach

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House Hinsdale

Family-oriented house with jacuzzi, terrace & garden | Suitable for remote work

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House Sandisfield

Waterfront oasis in heart of Berkshires

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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 2,301 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Stockbridge
House โˆ™ 6 guests โˆ™ 3 bedrooms

House with barbeque, garden & patio

Stockbridge, Berkshire County, Massachusetts, United States
This charming house rental in Stockbridge accommodates 8 guests and features a cozy fireplace for warm gatherings.
from $246
per night
(44)
View deal
Cabin Otis
Cabin โˆ™ 6 guests โˆ™ 2 bedrooms

Cottage with barbeque, garden & patio | Lake view

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 $318
per night
(19)
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House Sandisfield
House โˆ™ 6 guests โˆ™ 4 bedrooms

Vacation home with hot tub, patio & yard | Lake view

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 $363
per night
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Cabin Lanesborough
Cabin โˆ™ 5 guests โˆ™ 3 bedrooms

Cabin with jacuzzi, grill & terrace | Lake view | Suitable for remote work

Lanesborough, Berkshire County, Massachusetts, United States
This cozy cabin in Lanesborough accommodates 5 guests and features a relaxing hot tub for a perfect getaway.
from $313
per night
(165)
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House Williamstown
House โˆ™ 10 guests โˆ™ 3 bedrooms

Family-friendly vacation home with BBQ & patio | Mountain view | Perfect for remote work

Williamstown, Berkshire County, Massachusetts, United States
This house rental in Williamstown accommodates 10 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $453
per night
(35)
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House Hancock
House โˆ™ 7 guests โˆ™ 2 bedrooms

Vacation home with patio, pool & hot tub

Hancock, Berkshire County, Massachusetts, United States
This house rental in Hancock accommodates 7 guests and features a relaxing hot tub for your enjoyment.
from $212
per night
(2)
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House Lenox
House โˆ™ 6 guests โˆ™ 3 bedrooms

Family-oriented pleasant vacation home with barbecue, terrace & yard | Mountain view | Suitable for remote work

Lenox, Berkshire County, Massachusetts, United States
This house rental in Lenox accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $220
per night
(112)
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Cabin Windsor
Cabin โˆ™ 10 guests โˆ™ 1 bedroom

Cottage with barbecue

Windsor, Berkshire County, Massachusetts, United States
This cozy cabin in Windsor accommodates 10 guests and features convenient parking for your stay.
from $243
per night
(11)
View deal
House Lenox
House โˆ™ 17 guests โˆ™ 8 bedrooms

House with barbeque, terrace & yard | Mountain view

Lenox, Berkshire County, Massachusetts, United States
This house rental in Lenox accommodates 15 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $1,205
per night
(82)
View deal

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