Great Barrington Vacation Rentals

Compare 727 available properties from 16 providers
Great Barrington
Save up to 39%

Best Vacation Home Deals in Great Barrington

-37%
e.g. 9/15 - 9/22
House ∙ 5 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $150 $237
VRBO
4.8
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-19%
e.g. 9/22 - 9/29
House ∙ 3 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts, United States
from $217 $268
VRBO
5.0
View deal
-39%
e.g. 9/15 - 9/22
Apartment ∙ 4 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $133 $216
VRBO
4.9
View deal

Compare and find a dreamlike property from $59 per night by searching among the 727 properties being offered in Great Barrington. By comparing these vacation rentals, HomeToGo brings you the most economical offers as well as the highest rated properties in Great Barrington.

Recommended Vacation Rentals in Great Barrington

Rent a vacation accommodation in Great Barrington: from $60 per night

Apartment ∙ 4 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $133
VRBO
4.9
View deal
Apartment ∙ 4 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts, United States
from $133
VRBO
5.0
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $141
VRBO
4.9
View deal
Apartment ∙ 2 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts, United States
from $193
VRBO
4.0
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House ∙ 6 guests ∙ 2 bedrooms
Stockbridge, Berkshire County, Massachusetts, United States
from $315
HomeAway
4.8
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House ∙ 6 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $350
VRBO
4.9
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House ∙ 5 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $282
VRBO
4.5
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Motel ∙ 3 guests
Great Barrington, Berkshire County, Massachusetts, United States
from $106
Booking.com
4.2
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Vacation Homes With Fishing Spots Nearby

Fishing
House ∙ 6 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $318
VRBO
4.9
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Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts, United States
from $90
VRBO
4.9
View deal
Fishing
House ∙ 4 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $175
VRBO
4.9
View deal
Fishing
House ∙ 5 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $150
VRBO
4.8
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Vacation Rentals With a Fireplace

Fireplace
House ∙ 6 guests ∙ 2 bedrooms
New Marlborough, Berkshire County, Massachusetts, United States
from $170
VRBO
5.0
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Fireplace
House ∙ 6 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $138
VRBO
4.2
View deal
Fireplace
House ∙ 10 guests ∙ 4 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $293
HomeAway
4.8
View deal
Fireplace
House ∙ 10 guests ∙ 4 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $409
VRBO
4.9
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Best Dog-Friendly Rentals

Pet-friendly
House ∙ 5 guests ∙ 2 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $179
VRBO
4.9
View deal
Pet-friendly
House ∙ 3 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts, United States
from $217
VRBO
5.0
View deal
Pet-friendly
House ∙ 4 guests ∙ 2 bedrooms
New Marlborough, Berkshire County, Massachusetts, United States
from $158
HomeAway
4.6
View deal
Pet-friendly
House ∙ 7 guests ∙ 3 bedrooms
Great Barrington, Berkshire County, Massachusetts, United States
from $250
VRBO
5.0
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Popular Rental Amenities in Great Barrington

  • Internet (632)
  • Parking (611)
  • No smoking (609)
  • TV (568)
  • AC (526)
  • Yard (449)
  • Kitchen (442)
  • Microwave (380)
  • Washer (364)
  • Grill (344)
  • Fishing (338)
  • Dishwasher (334)
Accommodations can be narrowed down based on the amenities they offer. Above, you can see the number of properties that include a specific amenity in Great Barrington. Great Barrington is the perfect place to book a rental if you can't imagine a vacation without internet or you want to tune out with some TV time, as the most common amenities are "internet" and "TVs." Three features that are not often provided are "saunas," "Jacuzzis," and "pools."

Price and Availability Index Great Barrington

Vacation Rental Price Information in Great Barrington

The price graph will give you the nightly price average for the upcoming months of the year. Prices in a week of July (7/21 - 7/28) go up to $391 per night, which is the highest average price in the next 12 months. Conversely, the cheapest average prices are in a week of November (11/10 - 11/17).

Rental Availability Information in Great Barrington

Check how busy Great Barrington is with our availability graph. The week with the least available rentals is in August (8/4 - 8/11), with only 31% of the rentals available. Conversely, it is in May (5/11 - 5/18) that the highest percentage of rentals are available.

The Weather in Great Barrington

32°
16°
34°
16°
41°
23°
55°
34°
68°
46°
73°
54°
81°
59°
77°
55°
72°
48°
59°
39°
46°
28°
37°
25°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Great Barrington. During July, maximum temperatures go up to more than 80° However, temperatures can go lower than 15° in Great Barrington in January. Bring your umbrella in December, the rainiest month of the year!

In Great Barrington, house rentals are the most typical accommodation type. In addition, the median nightly price of house rentals in this destination is $406, and the average size is 2,590 ft². Moreover, this specific type of property is ideal for large groups, as most of the house rentals can host groups of 8. Bed & Breakfast rentals are the other most common property type in Great Barrington. These properties cost $305 per night on average and have an average size of 420 ft².

A vacation rental in Great Barrington: life is calling

Are you craving the green landscapes in Massachusetts? Vacation rentals in Great Barrington range from romantic cottages with beautiful views, to lakefront cabins, and even rustic log homes.

Show all 727 properties
Food & Drinks

The best local eats in Great Barrington

One of the highlights of Great Barrington is the Barrington Brewery & Restaurant, which not only offers you American bar food, but also a wide selection of delicious home brews. What better way to start off your vacation than by enjoying food and famous, local craft beer? Once you've sated your appetite, you must visit SoCo Creamery for the best ice cream in the Berkshires - there are lots of flavors to choose from, but the coconut and ginger are to die for!

Family Activities

Entertaining the kids: family fun in Great Barrington

If you are a family of skiiers, look no further than Ski Butternut, one of the most famous ski resorts in Great Barrington, located on Warner Mountain in the Berkshires. Offering stunning views of the alpine landscape, ski lessons, 2 terrain parks, and 22 trails, this is the best destination for winter family fun. Children who love hiking will enjoy Monument Mountain, which offers easy hikes through gorgeous terrain (particularly when the fall leaves are changing color). At Beartown State Forest, a scenic park with a fishing pond, you can see wildlife, enjoy winter sports, or take advantage of year-round hiking trails whenever you decide to visit.

Local Events

Renowned Berkshire festivals

The Annual Berkshires Arts Festival has been presenting art and fine crafts for over 30 years. Located right in Great Barrington, this festival has been consistently rated as one of the 10 Great Cultural Hotspots in Western Massachusetts. Travelers will find great food, exquisite arts & crafts, and a relaxed atmosphere for the whole family to enjoy. Great Barrington also proudly hosts the world-class Berkshire International Film Festival every year, featuring premier feature films, documentaries, shorts, and family films.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Great Barrington VRBO Vacation Rentals in Great Barrington HomeAway Vacation Rentals in Great Barrington TripAdvisor Vacation Rentals in Great Barrington VacationRentals.com Vacation Rentals in Great Barrington HouseTrip Vacation Rentals in Great Barrington FlipKey Vacation Rentals in Great Barrington Wimdu Vacation Rentals in Great Barrington 9flats.com Vacation Rentals in Great Barrington VaycayHero Vacation Rentals in Great Barrington PerfectPlaces.com Vacation Rentals in Great Barrington Homestay.com Vacation Rentals in Great Barrington only-apartments Vacation Rentals in Great Barrington Interhome Vacation Rentals in Great Barrington Bedycasa Vacation Rentals in Great Barrington Novasol Vacation Rentals in Great Barrington HomeEscape Vacation Rentals in Great Barrington

Vacation Destinations Near Great Barrington