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Great Barrington Vacation Rentals

Find 208 available offers from 5 partners
Great Barrington
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Farmhouse
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+

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.

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Best Vacation Home Deals in Great Barrington

Save up to 67%

House Great Barrington
Jan 5 - Jan 12
-60%
$781
$311 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful Vacation Home in Housatonic with Botanical Garden

5.0
Outstanding (16 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 2 - Dec 9
-67%
$357
$119 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Housatonic with Botanical Garden

5.0
Outstanding (14 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 2 - Dec 9
-62%
$221
$83 per night
House ∙ 4 guests ∙ 2 bedrooms

Vacation Home in Great Barrington with Grill

4.0
Very good (1 rating)
Great Barrington, Berkshire County, Massachusetts, United States
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Compare and find a dreamlike property from $83 per night by searching among the 208 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.

Top-Rated Rentals and Accommodations in Great Barrington

Book Vacation Rental Offers with the Highest User Rating

House Great Barrington
Dec 1 - Dec 8
$462 per night
House ∙ 10 guests ∙ 5 bedrooms

Nice Vacation Home in Great Barrington with Botanical Garden + Sunset View

5.0
Outstanding (76 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Cottage Great Barrington
Oct 12 - Oct 19
$214 per night
Cottage ∙ 3 guests ∙ 1 bedroom

Pleasant Cottage in Great Barrington with Botanical Garden + Glorious Views

5.0
Outstanding (52 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 1 - Dec 8
-37%
$508
$322 per night
House ∙ 8 guests ∙ 4 bedrooms

Lovely Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (24 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Recommended Vacation Rentals in Great Barrington

Find your perfect vacation rental in Great Barrington: from $83 per night

House Great Barrington
Mar 23 - Mar 30
-58%
$300
$125 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Great Barrington with Botanical Garden

4.7
Excellent (35 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
May 18 - May 25
$221 per night
House ∙ 5 guests ∙ 2 bedrooms

Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (15 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 2 - Dec 9
$295 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Great Barrington with Botanical Garden

4.9
Outstanding (83 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Apartment Great Barrington
Apr 13 - Apr 20
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Housatonic with Botanical Garden + Spectacular View

5.0
Outstanding (61 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 2 - Dec 9
$360 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Great Barrington with Botanical Garden

4.6
Excellent (10 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Apr 13 - Apr 20
-23%
$650
$499 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Great Barrington with Botanical Garden + Nature Views

5.0
Outstanding (12 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
May 4 - May 11
$350 per night
House ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home in Great Barrington with Botanical Garden

4.9
Outstanding (100 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 1 - Dec 8
-62%
$327
$123 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Great Barrington with Grill

Great Barrington, Berkshire County, Massachusetts, United States
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Cabin Great Barrington
Dec 2 - Dec 9
-28%
$400
$288 per night
Cabin ∙ 10 guests ∙ 3 bedrooms

Cabin in Great Barrington with Grill

Great Barrington, Berkshire County, Massachusetts, United States
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Budget-friendly Vacation Rentals in Great Barrington

Find Fantastic yet Inexpensive Offers

House Great Barrington
May 18 - May 25
-29%
$349
$248 per night
House ∙ 5 guests ∙ 3 bedrooms

House in Housatonic with Botanical Garden + Fantastic Views

5.0
Outstanding (47 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Dec 2 - Dec 9
-53%
$455
$212 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Great Barrington

5.0
Outstanding (22 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Feb 3 - Feb 10
$700 per night
House ∙ 15 guests ∙ 7 bedrooms

Historic Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (33 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Great Barrington by booking a vacation home with a fireplace.

House  Great Barrington
Dec 2 - Dec 9
-26%
$502
$373 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Great Barrington with Beautiful Fireplace

5.0
Outstanding (2 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
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House  Great Barrington
Jul 5 - Jul 12
$400 per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation Home in Housatonic with Yard & Grill

Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
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House  Great Barrington
Dec 16 - Dec 23
$223 per night
House ∙ 5 guests ∙ 3 bedrooms

Vacation Home in Great Barrington with Botanical Garden

Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Great Barrington and book a vacation rental with air conditioning.

House  Great Barrington
Jan 20 - Jan 27
$810 per night
House ∙ 14 guests ∙ 7 bedrooms

Lovely House in Great Barrington with Yard

5.0
Outstanding (2 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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House  Great Barrington
Oct 12 - Oct 19
-36%
$841
$542 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Housatonic with Botanical Garden

5.0
Outstanding (26 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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House  Great Barrington
Jan 6 - Jan 13
-59%
$924
$378 per night
House ∙ 14 guests ∙ 6 bedrooms

House in Housatonic with Grill + Degree Views

5.0
Outstanding (1 rating)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes in Great Barrington with their own private patios and balconies.

House  Great Barrington
Aug 24 - Aug 31
$234 per night
House ∙ 8 guests ∙ 2 bedrooms

House in Great Barrington with Marble Fireplace

4.7
Excellent (77 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
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House  Great Barrington
May 25 - Jun 1
-46%
$1,750
$940 per night
House ∙ 12 guests ∙ 4 bedrooms

House in Great Barrington with Private Pool

5.0
Outstanding (59 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
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House  Great Barrington
Jan 5 - Jan 12
-20%
$2,500
$2,000 per night
House ∙ 18 guests ∙ 6 bedrooms

Vacation Home in Great Barrington with Juliet Balcony + Mountain Views

5.0
Outstanding (2 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
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Popular Rental Amenities in Great Barrington

  • Pet-friendly (44)
  • WiFi (201)
  • Pool (64)
  • Air conditioning (195)
  • TV (183)
  • Kitchen (112)
  • Washing machine (122)
  • No smoking (147)
  • Fireplace (80)
  • Parking (17)
  • Dishwasher (91)
  • Grill (108)

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 travel with your pet or you need internet access during your vacation, as the most common amenities are "Pets allowed" and "Internet." Three features that are not often provided are "Detached," "Fenced," and "Crib."

The Weather in Great Barrington

max.
Min.
32°
16°
17 days 17
max.
Min.
34°
16°
18 days 18
max.
Min.
41°
23°
16 days 16
max.
Min.
55°
34°
15 days 15
max.
Min.
68°
46°
14 days 14
max.
Min.
73°
54°
14 days 14
max.
Min.
81°
59°
14 days 14
max.
Min.
77°
55°
11 days 11
max.
Min.
72°
48°
11 days 11
max.
Min.
59°
39°
16 days 16
max.
Min.
46°
28°
14 days 14
max.
Min.
37°
25°
20 days 20
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out our climate diagram to find the perfect month for your vacation. July is the warmest month in Great Barrington with average maximum temperatures of 81°. January is the coolest month, with average minimal temperature reaching 16°. The rainiest month is December while the driest month is August.

7-Day Weather Forecast in Great Barrington

Wed, 29 Nov
32°
26°

0%

4 h

7 mi/h

Thu, 30 Nov
37°
33°

0%

5 h

8 mi/h

Fri, 1 Dec
44°
35°

15%

0 h

5 mi/h

Sat, 2 Dec
41°
35°

10%

3 h

5 mi/h

Sun, 3 Dec
33°
33°

15%

0 h

4 mi/h

Mon, 4 Dec
35°
35°

15%

0 h

3 mi/h

Tue, 5 Dec
39°
37°

15%

0 h

11 mi/h

Accommodations for your vacation in Great Barrington

In Great Barrington, house rental are the most typical accommodation type. In addition, the median nightly price of house rental in this destination is $753, and the average size is 255 m². Moreover, this specific type of property is ideal for large groups, as most of the house rental can host groups of 9. Bed and breakfast rental are the other most common property type in Great Barrington. These properties cost $375 per night on average and have an average size of 40 m².
Where to find the best food in Great Barrington?

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!

What are the best activities for families in Great Barrington?

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.

What are the best events and festivals in Great Barrington?

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.

Information about vacation rentals in Great Barrington

🏡 Vacation rentals available 208 homes
💳 Possible discounts up to 67%
🌙 Nightly prices starting at $83
⭐ Popular amenities Pets allowed, Internet and Pool
🐾 Pet friendly homes 42 homes
🏊 Vacation rentals with pools 64 homes

Frequently Asked Questions

What is the typical nightly price for a vacation rental in Great Barrington?

The nightly price of accommodations in Great Barrington starts at $83. If you would like to stay in a house rental, the average price is $753 per night. A bed and breakfast rental Great Barrington will cost $375 per night on average.

How many vacation homes are available to book in Great Barrington?

Currently there are 208 vacation homes in Great Barrington to choose from and rent for your upcoming trip.

What are the most popular amenities for vacation rentals in Great Barrington?

If you're looking to book a vacation rental in Great Barrington, others search for accommodation with Pets allowed, Internet and Pool.

How many vacation rentals with a pool are there in Great Barrington?

There are 64 vacation rentals across 5 providers in Great Barrington.

Are dogs allowed in vacation rentals in Great Barrington?

Finding a vacation rental in Great Barrington that allows dogs is easy, with 42 pet-friendly available.

What's the best month to travel to Great Barrington?

If booking a vacation rental in Great Barrington, consider that rainy season is usually in December or February, with August often being the driest.

Find the perfect Great Barrington home to match your style

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