Bennington vacation rentals

We found 93 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of vacation rentals in Bennington that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include air conditioning and a pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Get rewards you won't find with any other major vacation rental platform

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Choose a vacation rental for your Bennington getaway

Experience the unique character of Bennington with a stay in a vacation home rental. One of the city's many top draws is its skiing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Bennington

Are you looking for attractions to visit while you're in the area? Venture out of your vacation home and experience everything that Bennington has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Crotched Mountain Ski and Ride Area (2.1 mi / 3.3 km)
  • Friendly Farm (10.6 mi / 17.1 km)
  • Pats Peak (12.6 mi / 20.4 km)
  • Monadnock State Park (13.6 mi / 21.8 km)
  • Stonebridge Golf Course (14.7 mi / 23.7 km)
  • Cathedral of the Pines (15.8 mi / 25.4 km)

Exploring the natural features in Bennington

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Bennington is a great place to get outside. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Pack Monadnock Mountain (9.5 mi / 15.3 km)
  • Contoocook River (13.4 mi / 21.6 km)
  • Monadnock State Park (13.6 mi / 21.8 km)
  • Nubanusit Lake (7.3 mi / 11.8 km)
  • Highland Lake (11.1 mi / 17.9 km)
  • Granite Gorge (15.1 mi / 24.3 km)

How to get to and around Bennington

The nearest airport is in Manchester-Boston Regional Airport (MHT), located 24.6 mi (39.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Concord, NH (CON-Concord Municipal), which is 25.1 mi (40.4 km) away.

Frequently asked questions

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

Campgrounds are the most popular kind of vacation rental in Bennington, according to our data. Even if you've got something bigger or smaller in mind, Vrbo has vacation homes in many sizes and shapes. Browse our many options to find your ideal fit.

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

Length of stay, property type and season are some factors that can determine the price of a vacation home. Simply enter your dates of travel to find your ideal escape. From cozy cabins to sprawling villas, all Vrbo vacation rentals offer terrific value.

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

Prices for beach houses in Bennington differ depending on the type and size of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to tailor your search by nearby activities, ratings, amenities and more.

Are there pet-friendly vacation rentals in Bennington?

With three properties that host four-legged guests, your furry friend can also come along on your Bennington break. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.

What are popular rental amenities in Bennington?

A garden, mountain views and nearby museums head the list of most popular rental amenities in Bennington. Whether you're heading away on your own, with your other half or a bunch of friends, Vrbo can help you find a vacation rental that fits your style with all the conveniences you're looking for.

Are there vacation rentals in Bennington that welcome kids?

Gather your whole crew for an epic adventure in Bennington at one of our three family-friendly properties. Lots of these stays provide amenities that are just perfect for getaways with the kids, including full kitchens, multiple bedrooms and outdoor spaces. Just click on the "Properties good for families" filter and select your favorite.

What are the top attractions for families in Bennington?

Keep the kids happy at these fantastic family-friendly attractions in Bennington:

  • The Monadnock Center for History and Culture
  • Greenfield State Park
  • Nubanusit Lake

Are there vacation rentals with WiFi in Bennington?

Bennington has two vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to checking emails, these Vrbo homes make it a breeze to get online.

How can I find vacation rentals with air conditioning in Bennington?

Decide on your travel dates and then use the filter tool to look for vacation rentals with air conditioning in Bennington on Vrbo. With two air-conditioned properties available, you can enjoy a comfy and cool stay.

How old do you have to be to rent a vacation rental in Bennington?

We recommend you check with the Bennington vacation home you're looking at on Vrbo as the minimum age varies. However, normally it's 16, 18 or 21.

How long can I rent a vacation rental in Bennington for?

It really depends on the Bennington property. To see all available options offering extended stays, simply enter your dates and guest number into Vrbo. You can enjoy having the entire place to yourself, as well as comforts such as a fully-equipped kitchen and a yard to play in. Be on the lookout for long-term stays that offer weekly or monthly discounts.

More Vacation Rentals ideas

People also search for