Vacation rentals in Great Barrington - HomeToGo base64Hash Vacation rentals in Great Barrington - HomeToGo

Vacation rentals in Great Barrington

Find 279 available house rentals from 9 partners
Anytime
Guests
Anytime
Guests

Top 15 Recommended vacation rentals in Great Barrington

Find your perfect vacation rental in Great Barrington from just $134 per night!

House Great Barrington
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented ample vacation home with grill | Water view

Great Barrington, Berkshire County, Massachusetts, United States
from $323
per night
Excellent(3 ratings)
from $323
per night
View deal
House Great Barrington
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped house with grill & patio | Lake view | Pets are welcome

Great Barrington, Berkshire County, Massachusetts, United States
from $336
per night
Good(109 ratings)
from $336
per night
View deal
House Great Barrington
House ∙ 9 guests ∙ 4 bedrooms

House with garden, grill & terrace

Great Barrington, Berkshire County, Massachusetts, United States
from $409
per night
Outstanding(43 ratings)
from $409
per night
View deal
House Great Barrington
House ∙ 6 guests ∙ 4 bedrooms

Family-friendly beautiful vacation home with yard, grill & patio | Lake view

Great Barrington, Berkshire County, Massachusetts, United States
from $291
per night
Outstanding(80 ratings)
from $291
per night
View deal
House Great Barrington
House ∙ 14 guests ∙ 4 bedrooms

Fully equipped vacation home with patio, grill & garden | Mountain view | Dogs allowed

Great Barrington, Berkshire County, Massachusetts, United States
from $426
per night
Outstanding(56 ratings)
from $426
per night
View deal
House Great Barrington
House ∙ 12 guests ∙ 6 bedrooms

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

Great Barrington, Berkshire County, Massachusetts, United States
from $444
per night
Outstanding(142 ratings)
from $444
per night
View deal
House Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, barbeque & garden | Nature view

Great Barrington, Berkshire County, Massachusetts, United States
from $372
per night
Outstanding(57 ratings)
from $372
per night
View deal
House Great Barrington
House ∙ 12 guests ∙ 4 bedrooms

House with yard, patio & grill

Great Barrington, Berkshire County, Massachusetts, United States
from $879
per night
Outstanding(64 ratings)
from $879
per night
View deal
House Great Barrington
House ∙ 15 guests ∙ 7 bedrooms

Child-friendly vacation home with grill & garden | Pets are welcome

Great Barrington, Berkshire County, Massachusetts, United States
from $734
per night
Outstanding(40 ratings)
from $734
per night
View deal
Cottage Great Barrington
Cottage ∙ 3 guests ∙ 1 bedroom

Family-oriented pleasant cottage with private pool, BBQ & garden | Nature view | Suitable for remote work | Pets allowed

Great Barrington, Berkshire County, Massachusetts, United States
from $299
per night
Outstanding(67 ratings)
from $299
per night
View deal
House Great Barrington
House ∙ 6 guests ∙ 4 bedrooms

Children-friendly pleasant vacation home with grill, yard & terrace | Nature view | Pet-friendly

Great Barrington, Berkshire County, Massachusetts, United States
from $403
per night
Outstanding(8 ratings)
from $403
per night
View deal
House Great Barrington
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped vacation home with pool & grill | Pets allowed

Great Barrington, Berkshire County, Massachusetts, United States
from $415
per night
Outstanding(2 ratings)
from $415
per night
View deal
House Great Barrington
House ∙ 6 guests ∙ 3 bedrooms

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

Great Barrington, Berkshire County, Massachusetts, United States
from $376
per night
Outstanding(40 ratings)
from $376
per night
View deal
House Great Barrington
House ∙ 8 guests ∙ 4 bedrooms

House with yard, terrace & hot tub

Great Barrington, Berkshire County, Massachusetts, United States
from $353
per night
Outstanding(52 ratings)
from $353
per night
View deal
House Great Barrington
House ∙ 11 guests ∙ 3 bedrooms

Fully equipped vacation home with garden & barbecue | Pets are welcome

Great Barrington, Berkshire County, Massachusetts, United States
from $321
per night
Outstanding(12 ratings)
from $321
per night
View deal

Vacation rentals and apartments with air conditioning

House  Great Barrington
from $370
per night
House ∙ 9 guests ∙ 5 bedrooms

Vacation home with terrace, garden & BBQ

5.0
Outstanding(43 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
View deal
Cabin  Great Barrington
from $354
per night
Cabin ∙ 10 guests ∙ 4 bedrooms

Child-friendly nice cabin with terrace & garden | Mountain view | Pet-friendly

4.9
Outstanding(20 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
View deal
House  Great Barrington
from $357
per night
House ∙ 10 guests ∙ 5 bedrooms

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

4.2
Very good(16 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Air conditioning
View deal
See all offers

Vacation rentals with a balcony

Apartment  Great Barrington
from $225
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Rental apartment with terrace, BBQ & yard | Mountain view

5.0
Outstanding(65 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
View deal
House  Great Barrington
from $627
per night
House ∙ 8 guests ∙ 4 bedrooms

House with yard, barbecue & sauna

5.0
Outstanding(7 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
View deal
House  Great Barrington
from $383
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with BBQ & garden | Nature view | Good for workation

4.5
Excellent(5 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Balcony
View deal
See all offers

Vacation Rentals With Fireplaces

House  Great Barrington
from $664
per night
House ∙ 10 guests ∙ 4 bedrooms

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

4.8
Outstanding(20 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
View deal
House  Great Barrington
from $959
per night
House ∙ 16 guests ∙ 5 bedrooms

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

5.0
Outstanding(63 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
View deal
House  Great Barrington
from $489
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented vacation home with patio & grill

Great Barrington, Berkshire County, Massachusetts, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Great Barrington

Save up to 22%

House Great Barrington
-22%
$417
from $325
per night
House ∙ 4 guests ∙ 2 bedrooms

House with terrace & grill | Beach view

4.8
Outstanding(23 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal

Choose a rental that fits your criteria among the 279 great rentals from 9 providers in Great Barrington. Using HomeToGo you can easily search and compare the offers of each available rental to find the best price and save up to 10%.

Budget-friendly Vacation Rentals in Great Barrington

Find Fantastic yet Inexpensive Offers

House Great Barrington
from $315
per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with patio & grill | Lake view

3.6
Good(109 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal
House Great Barrington
from $359
per night
House ∙ 8 guests ∙ 4 bedrooms

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

4.5
Excellent(9 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal
House Great Barrington
from $476
per night
House ∙ 8 guests ∙ 4 bedrooms

House with barbeque & yard

5.0
Outstanding(4 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal

Top-Rated Rentals and Accommodations in Great Barrington

Book Vacation Rental Offers with the Highest User Rating

House Great Barrington
from $479
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped ample vacation home with terrace, yard & BBQ | Nature view | Perfect for remote work | Pets allowed

5.0
Outstanding(48 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal
House Great Barrington
from $383
per night
House ∙ 8 guests ∙ 3 bedrooms

Child-friendly house with garden, BBQ & terrace | Mountain view | Perfect for remote work | Pets allowed

4.6
Excellent(37 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal
Apartment Great Barrington
from $208
per night
Apartment ∙ 4 guests ∙ 2 bedrooms

Nice holiday apartment with barbeque

4.7
Excellent(33 ratings)
Great Barrington, Berkshire County, Massachusetts, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Great Barrington

  • Pet-friendly (81)
  • WiFi (272)
  • Pool (85)
  • Air conditioning (259)
  • TV (224)
  • Kitchen (156)
  • Washing machine (155)
  • No smoking (256)
  • Fireplace (106)
  • Parking (15)
  • Dishwasher (96)
  • Grill (107)

One-third of the accommodations offer a pool, which makes Great Barrington a great place for travelers looking to make a splash. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 9, as that is the number of people they can welcome on average. more than half of Great Barrington's properties with pools are within two miles of water, choose between some pool time or waterfront moments.

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.

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.

Information about vacation rentals in Great Barrington

🏡 Vacation rentals available 279 rentals
🌙 Nightly prices starting at $134
⭐ Popular amenities Pets allowed, Internet and Pool
🐾 Pet friendly homes 80 homes
🏊 Vacation rentals with pools 85 homes
32,605 reviews
Great Barrington vacation rentals have an average rating of 4.5/5 on 32,605 reviews left by travelers.

Frequently Asked Questions

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

The average accommodation in Great Barrington is priced at $134 per night. Nightly prices for house rentals are $704 on average. Bed and breakfast rentals in Great Barrington cost on average $318 per night.

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

Currently there are 279 rentals to choose from for your next trip.

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

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

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

Great Barrington offers 85 Hotel room and Motel on offer to rent.

Are dogs allowed in vacation rentals in Great Barrington?

If you are traveling with a pet in Great Barrington - 29% of vacation homes are pet-friendly.

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

When choosing a vacation rental in Great Barrington, consider that rainy season is typically in December or February, with August often being the driest.

Most Popular Destinations

Show more

Top cities to visit

image-tag