Discover a selection of 414 holiday rentals in Great Barrington that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 211 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 theatre scene are just some of the reasons to come on holiday to Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. Whether you're planning a family holiday, romantic stay or trip with friends, holiday 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 holiday rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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

Travellers 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 40.68 inches and temperatures average -10°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 holiday in Great Barrington. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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

Travelling 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 centre. 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.

Can I find a vacation rental around Great Barrington?

Yes, our 2021 property listings offer a large selection of 414 vacation rentals near Great Barrington. From 332 houses to 56 cabins, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Great Barrington for a holiday or a weekend are on Vrbo.