Great Barrington vacation rentals

We found 589 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Select from 100 homes, 19 cottages, and other vacation rentals in Great Barrington to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, which might include air conditioning and a pool. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
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The lively city of Great Barrington awaits you

The area's live music and theater scene are just a few of the reasons to vacation in Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Great Barrington

Do you want to discover attractions to see while you're in the area? You'll be sure to enjoy Great Barrington for its hiking and skiing. Venture out of your vacation home and experience everything that makes Great Barrington a fun spot to vacation. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Bousquet Ski Area (15.7 mi / 25.3 km)
  • Lake Taghkanic State Park (18.9 mi / 30.4 km)
  • Les Trois Emme Winery (5.2 mi / 8.4 km)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Great Barrington. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Housatonic River Walk (0.1 mi / 0.2 km)
  • Naumkeag Museum (6.9 mi / 11.1 km)
  • Bash Bish Falls State Park (8.9 mi / 14.3 km)
  • The Mount (10.5 mi / 16.8 km)
  • Taconic State Park (11.7 mi / 18.8 km)
  • October Mountain State Forest (14.3 mi / 23 km)

Seasonal weather averages in Great Barrington

Travelers enjoy Great Barrington for its skiing. To make the most of the cold weather activities, you might consider visiting in March, January, February or November, when snowfall averages 13 inches and temperatures average 28°F.

Transportation options to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away.

Frequently asked questions

What is the best area to stay in Great Barrington when booking a vacation rental?

One of the more in-demand destinations to choose your Vrbo vacation rental in Great Barrington is Egremont. Set up home here and enjoy its big-ticket attractions, including Catamount Ski Area and Jug End State Reservatio.

What is the most popular type of vacation rental accommodation in Great Barrington?

Houses are the most popular style of vacation rental in Great Barrington, according to our data. Even if you've got a different idea in mind, Vrbo has properties in many shapes and sizes. Look through our options to find your perfect pad.

How much does it cost to rent a vacation rental in Great Barrington?

Different things can determine what you'll pay for your vacation rental in Great Barrington, like the type of property, season and length of stay. However, all our vacation homes have one thing in common — amazing value. Just enter your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Great Barrington?

When you travel and the style and size of the property will influence how much you'll pay for your beachside vacation rental. Put in your Great Barrington travel dates to see your options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you want.

Are there pet-friendly vacation rentals in Great Barrington?

With 39 properties that host four-legged guests, your happy hound can join in on your Great Barrington getaway. Use our filter tool to browse our pet-friendly vacation rentals and find the pawfect pad on Vrbo.

Can I rent a house with a pool in Great Barrington?

Grab your swimsuit and pool noodle, because there are four houses with a private pool in Great Barrington. Kick back at one of these popular vacation homes and every day can be a pool day. Simply enter your dates into Vrbo, then check the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Great Barrington?

When it comes to rental amenities that guests are searching for in Great Barrington, a swimming pool, an electric car charging station and nearby museums rank the highest. With Vrbo vacation homes, you'll discover options to suit your style and taste, whether you're going on a trip with your partner, your friends or even pets.

Are there large group vacation rentals in Great Barrington?

Great Barrington has six vacation properties that can accommodate 10 or more guests. These stays come with the space and privacy you need to share good times with your favorite people.

Are there vacation rentals in Great Barrington that welcome kids?

Bring the entire family together for an unforgettable adventure in Great Barrington at one of our 39 family-friendly vacation homes. Many of these stays come with conveniences that are ideally suited to trips with the kids, such as laundry facilities, extra bedrooms and outdoor spaces. Just check the "Properties good for families" filter and choose your favorite option.

What are the top attractions for families in Great Barrington?

Keep your kids busy at these fantastic family-friendly attractions in Great Barrington:

  • Umpachene Falls Park
  • Norman Rockwell Museum
  • Bash Bish Falls State Park

Are there one-bedroom vacation rentals in Great Barrington?

Yes, you can pick from three one-bedroom rentals in Great Barrington. Whether you want a cozy cottage or an upmarket condo, Vrbo's one-bedroom rentals are ideal if you don't require lots of room. One of the best things about having your own place? You won't ever have to share your vacation with strangers.

Can I find two-bedroom vacation rentals in Great Barrington?

Gather your loved ones and enjoy total privacy and comfort in one of the 10 two-bedroom vacation properties Great Barrington has to offer.

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