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Great Barrington Vacation Rentals

Find 244 available offers from 13 partners
Great Barrington
Anytime
Guests
Great Barrington
Anytime
Guests

Popular Filters to find the Perfect Home Rental in Great Barrington

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Great Barrington rental with full kitchen.

Apartment  Great Barrington
Aug 17 - Aug 24
$355 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Rental Apartment in Great Barrington

Great Barrington, Berkshire County, Massachusetts, United States
Kitchen
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House  Great Barrington
Sep 21 - Sep 28
-50%
$1,054
$531 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Great Barrington with Grill, Yard & Patio

Great Barrington, Berkshire County, Massachusetts, United States
Kitchen
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House  Great Barrington
Jul 7 - Jul 14
$430 per night
House ∙ 11 guests ∙ 3 bedrooms

Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (2 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Kitchen
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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
Sep 16 - Sep 23
-23%
$458
$351 per night
House ∙ 9 guests ∙ 4 bedrooms

Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (40 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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House  Great Barrington
Sep 21 - Sep 28
$883 per night
House ∙ 16 guests ∙ 5 bedrooms

Vacation Home in Great Barrington with Private Parking

5.0
Outstanding (55 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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House  Great Barrington
Apr 27 - May 4
$333 per night
House ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (99 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Great Barrington accommodation with high-speed internet.

House  Great Barrington
Jun 1 - Jun 8
-26%
$406
$302 per night
House ∙ 10 guests ∙ 4 bedrooms

House in Great Barrington with Wood-Burning Fireplace + Incredible Views

3.7
Good (110 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Internet
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House  Great Barrington
Sep 21 - Sep 28
$347 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (46 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Internet
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House  Great Barrington
Sep 21 - Sep 28
$471 per night
House ∙ 8 guests ∙ 3 bedrooms

Pleasant Vacation Home in Great Barrington with Large Patio

5.0
Outstanding (37 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Internet
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Best Vacation Home Deals in Great Barrington

Save up to 39%

House Great Barrington
Jul 20 - Jul 27
-25%
$729
$545 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Great Barrington with Yard & Grill

5.0
Outstanding (1 rating)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
May 4 - May 11
-39%
$499
$303 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful Vacation Home in Great Barrington with Yard, Grill & Patio

4.9
Outstanding (91 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Apr 27 - May 4
-31%
$407
$279 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Great Barrington with Wood-Burning Fireplace + Floor-To-Ceiling Views

3.7
Good (110 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Compare and find a dreamlike property from $128 per night by searching among the 244 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

Find your perfect vacation rental in Great Barrington: from $128 per night

House Great Barrington
Jul 13 - Jul 20
$400 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Great Barrington with Botanical Garden + Mountain Views

5.0
Outstanding (27 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Jul 7 - Jul 14
$850 per night
House ∙ 15 guests ∙ 7 bedrooms

Historic Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (42 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Cottage Great Barrington
Apr 27 - May 4
-26%
$507
$377 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Pleasant Cottage in Great Barrington with Grill

Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Jul 20 - Jul 27
$367 per night
House ∙ 6 guests ∙ 4 bedrooms

House in Great Barrington

5.0
Outstanding (21 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Jun 1 - Jun 8
$312 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Great Barrington with Grill & Patio

Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Jun 15 - Jun 22
$428 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Great Barrington with Botanical Garden + Spectacular Views

4.9
Outstanding (136 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Apartment Great Barrington
Jul 27 - Aug 3
$161 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Wonderful Rental Apartment in Great Barrington with Botanical Garden

4.8
Outstanding (51 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
May 13 - May 20
$514 per night
House ∙ 10 guests ∙ 4 bedrooms

Beautiful Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (47 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Aug 17 - Aug 24
$475 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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Budget-friendly Vacation Rentals in Great Barrington

Find Fantastic yet Inexpensive Offers

House Great Barrington
Jun 1 - Jun 8
$349 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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Cottage Great Barrington
Jan 28 - Feb 4
$885 per night
Cottage ∙ 12 guests ∙ 5 bedrooms

Cottage in Great Barrington with Grill

Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Jun 30 - Jul 7
$441 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Great Barrington with Patio, Grill & Yard

5.0
Outstanding (2 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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Top-Rated Rentals and Accommodations in Great Barrington

Book Vacation Rental Offers with the Highest User Rating

Apartment Great Barrington
Oct 5 - Oct 12
$175 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental Apartment in Housatonic with Botanical Garden + Spectacular View

5.0
Outstanding (62 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Aug 3 - Aug 10
$1,500 per night
House ∙ 12 guests ∙ 5 bedrooms

Pleasant Vacation Home in Great Barrington with Botanical Garden

5.0
Outstanding (62 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
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House Great Barrington
Mar 29 - Apr 5
-34%
$458
$305 per night
House ∙ 9 guests ∙ 4 bedrooms

House in Great Barrington with Botanical Garden

5.0
Outstanding (40 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Free cancellation
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Popular Rental Amenities in Great Barrington

  • Pet-friendly (44)
  • WiFi (238)
  • Pool (75)
  • Air conditioning (233)
  • TV (217)
  • Kitchen (119)
  • Washing machine (122)
  • No smoking (235)
  • Fireplace (91)
  • Parking (18)
  • Dishwasher (98)
  • Grill (105)

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 bring your pet everywhere or you can't imagine a vacation without internet, 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

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32°
16°
17 days 17
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34°
16°
18 days 18
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41°
23°
16 days 16
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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

Tue, 16 Apr
57°
55°

0%

6 h

11 mi/h

Wed, 17 Apr
57°
53°

0%

4 h

4 mi/h

Thu, 18 Apr
41°
41°

15%

0 h

8 mi/h

Fri, 19 Apr
57°
55°

15%

0 h

5 mi/h

Sat, 20 Apr
53°
50°

5%

3 h

14 mi/h

Sun, 21 Apr
50°
50°

5%

1 h

9 mi/h

Mon, 22 Apr
55°
53°

10%

5 h

4 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 $703, and the average size is 247 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 $385 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 246 rentals
💳 Possible discounts up to 40%
🌙 Nightly prices starting at $130
⭐ Popular amenities Pets allowed, Internet and Pool
🐾 Pet friendly homes 47 homes
🏊 Vacation rentals with pools 74 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 $130. If you would like to stay in a house rental, the average price is $703 per night. A bed and breakfast rental Great Barrington will cost $385 per night on average.

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

Currently there are 246 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 74 vacation rentals across 13 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 47 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.

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