Discover a selection of 1,000 vacation rentals in Bennington 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 WiFi and swimming pools. Prices start at $128 per night, and houses and cabins are popular options for a stay in Bennington. Either way, you'll find a rental for everyone's needs.
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Destination guide

Why people love visiting friendly Bennington

The area's museums and monuments are just a few of the reasons to vacation in Bennington. Well known for its shopping, university setting and restaurants, this welcoming 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

Activities and attractions in Bennington

Are you looking for attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that makes Bennington a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Prospect Mountain Cross-Country Ski Center (6.1 mi / 9.8 km)
  • Clarksburg State Park (11.7 mi / 18.9 km)
  • Waubeeka Golf Links (15.4 mi / 24.9 km)
  • Haystack Golf and Country Club (15.7 mi / 25.3 km)
  • Mount Snow (16.6 mi / 26.8 km)
  • Mount Snow Golf Course (17.2 mi / 27.7 km)
Natural features

Exploring the natural landscape of Bennington

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Bennington. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Harmen Hills Trail (4.1 mi / 6.7 km)
  • Howard Park (4.9 mi / 7.8 km)
  • Lake Shaftsbury State Park (10 mi / 16.1 km)
  • Clarksburg State Park (11.7 mi / 18.9 km)
  • Natural Bridge State Park (13.2 mi / 21.3 km)
  • Western Gateway Heritage State Park (13.3 mi / 21.5 km)
How to get there

How to get to and around Bennington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 31.7 mi (51 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Albany, NY (ALB-Albany Intl.), which is 32.4 mi (52.1 km) away.

How many vacation rentals are available around Bennington?

Our 2021 property listings offer a large selection of 937 vacation rentals around Bennington. From 660 house rentals to 102 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.