Discover a selection of 407 vacation rentals in Great Barrington that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $160 per night, and houses and cabins are popular options for a stay in Great Barrington. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Great Barrington
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Destination guide

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 cafés, this scenic city won't disappoint. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities

Activities and attractions in and around Great Barrington

Are you searching for attractions to see while you're in town? You'll be sure to enjoy Great Barrington for its hiking and skiing. Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (1.2 mi / 2 km)
  • Les Trois Emme Winery (4 mi / 6.5 km)
  • Dry Hill (5.1 mi / 8.3 km)
  • Questing (5.9 mi / 9.5 km)
  • Catamount Ski Area (7 mi / 11.2 km)
  • Umpachene Falls Park (7.1 mi / 11.5 km)
Weather

Seasonal weather averages in Great Barrington

Travelers enjoy Great Barrington for its skiing. If you're interested in winter sports, you might consider visiting in February, March, December or January, when snowfall averages 16.01 inches and temperatures average 14°F.

Natural features

Exploring the natural features in Great Barrington

Whether you're an outdoor enthusiast 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 a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Lake Mansfield Park (1.8 mi / 2.9 km)
  • Beartown State Forest (5.2 mi / 8.3 km)
  • Umpachene Falls Park (7.1 mi / 11.5 km)
  • Tyringham Cobble (7.4 mi / 12 km)
  • Berkshire Botanical Garden (8 mi / 12.9 km)
  • Taconic Trail State Park (10 mi / 16.2 km)
How to get there

Traveling to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.8 mi (27.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Hudson, NY (HCC-Columbia County), which is 20.3 mi (32.7 km) away.

How many vacation rentals are available around Great Barrington?

Our 2021 property listings offer a large selection of 407 vacation rentals around Great Barrington. From 325 house rentals to 54 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.