Discover a selection of 1,000 vacation rentals in Bennington, VT 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 kitchens. Prices start at $143 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.
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 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, VT?

Our 2020 property listings offer a large selection of 927 vacation rentals around Bennington. From 475 house rentals to 61 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Bennington?

Unforgiving and mysterious, mountains are among the most ruggedly spectacular natural wonders on the planet. If you've ever wanted to experience high-altitude living, you've come to the right place. Vrbo has 403 mountain getaway rentals available. Open to other ideas? Vrbo has loads of other rental options to take a look at, including:

  • 198 mountainside vacation rentals.
  • 173 rural vacation rentals.
  • 151 village vacation rentals.

Can I rent a house in Bennington?

If you're after a home away from home this trip, renting an entire house is a terrific idea. You and your group will have ample space for all sorts of getaway activities. There are 479 houses listed on Vrbo. Prices start from $73 a night. If that doesn't match your squad's style, we've got a range of other rental options available, such as:

  • Condo: 164 vacation homes. Prices start from $60 per night.
  • Townhome: 91 vacation homes. Prices start from $100 per night.
  • Hotel: 47 vacation homes. Prices start from $19 per night.

Can I stay in Bennington in a large group?

It can be hard finding the time to spend with your nearest and dearest. A group vacation is an ideal way to be reunited. If you were planning to kick back together, Vrbo has options for you. 78 house vacation homes are available. At the moment, they're the most popular choice here for big groups. The rental options that are perfect for large numbers in this area include:

  • On the hunt for vacation homes that can sleep 8 vacationers? We have 166 that will fit the bill. The prices start from $100 per night.
  • If you've got 6 in your party, you'll be happy to hear that there are 165 vacation homes that are perfect. You can get one for as little as $60 a night.
  • Searching for properties for rent to suit 10 guests? You'll be delighted to find out we have 144 that will fit the bill. You can book one for as little as $97 a night.

You and all your besties will be more than satisfied when you arrange your Bennington vacation with us!

Where are the cheapest rentals in Bennington?

Pint-sized hotel rooms are no place to spend those precious vacation moments! Explore our value-for-money rentals now and ensure everyone in your group has enough room to spread out. North Bennington is a fantastic area to check out if you want to keep your budget under control. Vrbo has 3 rentals, and the average price is a very affordable $195 per night. Williamstown is another place worth considering. We've got 24 rentals here, and the average price is around $317 per night.

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