Great Barrington Vacation Rentals - HolidayHomes base64Hash Great Barrington Vacation Rentals - HolidayHomes

Great Barrington Vacation Rentals

Browse 227 available vacation homes and compared across 7 trusted partners

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Top-Rated Vacation rentals in Great Barrington

Book the highest-rated Great Barrington 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.
House Great Barrington

Family-friendly vacation home with patio, yard & hot tub | Suitable for remote work

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House Great Barrington

Secluded Forest Sanctuary • Outdoor Living, Yard, Views | Half Moon by AvantStay

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House Great Barrington

Vacation home with BBQ, terrace & jacuzzi | Lake view | Suitable for remote work

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Cabin Great Barrington

Romantic Berkshires Cottage - Stunning Views, Pool

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House Great Barrington

House with yard, patio & grill

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House Great Barrington

House with terrace, barbeque & garden

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House Great Barrington

House with yard, terrace & barbecue

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House Great Barrington

Fully equipped pleasant house with BBQ, terrace & yard | Suitable for remote work

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House Great Barrington

House with garden & barbecue | Nature view

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House Great Barrington

A Fun Farmhouse Near Ski Butternut

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House Great Barrington

Forest Views, Enclosed Patio in Secluded Modern Home Woodland Zen by AvantStay

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House Great Barrington

Vacation home with barbeque, hot tub & terrace | Nature view | Good for workation

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House Great Barrington

Family-oriented lovely vacation home with terrace, yard & barbeque | Nature view | Good for workation

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House Great Barrington

House with barbeque & terrace | Lake view | Suitable for remote work

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House Great Barrington

House with garden | Nature view

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Top 15 most Recommended Vacation Rentals in Great Barrington

Discover your ideal Great Barrington vacation rental with real-time comparisons of 227 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 Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

Child-friendly house with private pool & barbecue | Perfect for remote work | Dogs allowed

Great Barrington, Berkshire County, Massachusetts, United States
Spacious house rental in Great Barrington for 8 guests featuring a cozy fireplace and ample parking.
from $452
per night
(7)
View deal
House Great Barrington
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly lovely house with patio, garden & BBQ

Great Barrington, Berkshire County, Massachusetts, United States
Charming house rental in Housatonic for 6 with a cozy fireplace and a spacious yard for family-friendly outdoor fun.
from $183
per night
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House Great Barrington
House ∙ 9 guests ∙ 4 bedrooms

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

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Housatonic accommodates 9 guests and features a private pool for a relaxing getaway.
from $1,012
per night
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House Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbeque, patio & yard | Nature view | Good for workation

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 8 guests and features a family-friendly yard for outdoor activities.
from $364
per night
(21)
View deal
House Great Barrington
House ∙ 10 guests ∙ 4 bedrooms

Family-friendly house with grill, garden & terrace | Pets allowed

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 10 guests and features a spacious yard perfect for family gatherings.
from $546
per night
(21)
View deal
House Great Barrington
House ∙ 6 guests ∙ 3 bedrooms

House with barbecue, patio & yard

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 6 guests and features a spacious yard for outdoor relaxation.
from $666
per night
(5)
View deal
House Great Barrington
House ∙ 9 guests ∙ 4 bedrooms

Vacation home with barbeque & garden

Great Barrington, Berkshire County, Massachusetts, United States
This house rental in Great Barrington accommodates 9 guests and features a cozy fireplace for a warm, inviting atmosphere.
from $405
per night
(4)
View deal
Apartment Great Barrington
Apartment ∙ 4 guests ∙ 2 bedrooms

Nice holiday apartment with barbeque

Great Barrington, Berkshire County, Massachusetts, United States
This apartment rental in Great Barrington accommodates 4 guests and features a convenient kitchen for your culinary needs.
from $141
per night
(96)
View deal
Apartment Great Barrington
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with terrace, BBQ & yard | Nature view

Great Barrington, Berkshire County, Massachusetts, United States
This cozy apartment rental in Housatonic accommodates 4 guests and features a charming fireplace for a warm atmosphere.
from $214
per night
(73)
View deal

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