Discover a selection of 1,500 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 swimming pools. Prices start at $97 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.
Top rated rentals — Bennington
Destination guide

Adventurous Bennington will entice you

Enjoy the museums and other features of Bennington. This city's skiing, mountain views and hiking draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Things to do

Sightseeing in and around Bennington

Do you want to discover attractions to visit in the city? Travelers enjoy Bennington for its skiing, hiking and golfing. Venture out of your cozy vacation rental and experience everything that makes Bennington a fun spot to vacation. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Mount Snow (15.7 mi / 25.3 km)
  • Stratton Mountain Resort (21.5 mi / 34.6 km)
  • The Hermitage Golf Club (16.5 mi / 26.6 km)
  • Mount Snow Golf Course (17.9 mi / 28.9 km)
  • Willard Mountain (18.2 mi / 29.2 km)
  • Golf Club at Equinox (20.6 mi / 33.1 km)

Seasonal weather averages in Bennington

Bennington is well known for its skiing. If you've planned your trip around snowy activities, consider visiting in February, January, March or December, when snowfall averages 9 inches and temperatures average 27°F.

Natural features

Exploring the mountains and other natural features in Bennington

Whether you're an active traveler or just want to take in the scenery, Bennington is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Taconic Lake (11.5 mi / 18.5 km)
  • Natural Bridge State Park (13.7 mi / 22 km)
  • Grafton Lakes State Park (14.1 mi / 22.7 km)
  • Mount Equinox (16.9 mi / 27.2 km)
  • Mount Greylock (17.2 mi / 27.6 km)
  • Brodie Mountain (17.2 mi / 27.7 km)
How to get there

Traveling to and around Bennington

Fly into Albany Intl. Airport (ALB), the closest airport, 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 Pittsfield, MA (PSF-Pittsfield Municipal), which is 31.9 mi (51.4 km) away.

What are the top vacation rentals in or near Bennington?

Whether you're looking for an intimate retreat for you and your love or a sprawling house to fit all your friends, you'll find some top vacation rentals in and around Bennington. Here are a couple to get you inspired:

  • "Historic Renovated Barn At Boorn Brook Farm" is a hit with guests. Around 20 miles from Bennington, it has 2 bedrooms and lots of handy amenities, including a hair dryer and a fridge.
  • "Charming Vermont Home On 7 Acres W" also promises a memorable escape, offering 5 bedrooms, a porch, golf and more. It's around 25 miles from Bennington.

For even more great options, use the search bar at the top of the page to find the perfect Bennington vacation rental for you.

What are the best tiny house vacation rentals in or near Bennington?

Punching far above its weight when it comes to character and ingenuity, a tiny house vacation rental in Bennington promises big adventure. Power down all your tech and turn your focus to nature at one of these pocket-sized stays:

  • Leave the world behind and disappear to "Cozy Lakeside Tiny Home, Near Skiing". This property in Whitingham packs plenty of comforts into its cozy space, such as a kitchen and a firepit.
  • Alternatively, get comfy at "Cheerful Tiny Home Cabin Near Hiking". Situated in Townshend, this wee gem comes with towels and internet services.

Can I find log cabins to rent in or near Bennington?

There's something so cozy about hunkering down in a log cabin with a cup of tea and a good book. Leave the hustle and bustle of life behind and spend a few nights or longer at one of these log cabins in Bennington:

  • Plonk your bags down at "Brand New Custom Log Cabin In The Green Mtn Forest" in Searsburg and during your waking hours enjoy mountain biking and hiking and biking and your nights relaxing in comfort in your cozy cabin.
  • Looking for a Manchester Center log cabin with access to exciting outdoor activities like cross-country skiing and golf? You'll be very happy with "Luxurious Log Cabin Nestled In Private Meadow".

What are the top-rated vacation rentals for weekend getaways in or near Bennington?

Nothing tops squeezing in a quick trip to dust away the cobwebs. Pack your overnight bag and enjoy a breather at one of these enticing weekend getaways in and around Bennington:

  • Located 16 miles to the east of central Bennington, "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow" is a great fit for nature lovers and adventurous types. Find your way to nearby outdoor attractions, such as Winhall River and Lowell Lake State Park. If you're up for more, try mountain biking or golf.
  • Alternatively, leave your stresses behind at "True Ski In/ski Out Updated 3 Bedroom End Unit Directly On Mount Snow". Stay in and chill out, or head out and try your hand at some hiking and biking and horse riding. When it's time to explore more of the area, organize a visit to Fort Dummer State Park and American Express Ski Lift. This terrific vacation rental is around 16 miles east of Bennington.

Can I find studio apartments for rent in and around Bennington?

Typically compact, economical and conveniently located, it's not difficult to fall for the appeal of a studio apartment. Get cozy in one of these options and appreciate Bennington up close:

  • Explore the world around you from "Romantic Private Vermont Cottage". This vacation rental is a fantastic base for seeing the sights and offers amenities including a nearby laundromat and shopping.
  • Another great option is "Great Place To Get Away And Have Clean Fresh Air Surround You". Make the most of a fridge, WiFi and other amenities during your getaway.

With the moolah you save on your studio apartment, you'll be able to explore more of Bennington. Cultural attractions like Helen Day Art Center and T.W. Wood Art Gallery will help you get a feel for the character of this destination.

Can I find short term rentals in or near Bennington?

Short-term rentals aren't hard to find in and around Bennington. Chill out for the weekend in a cool condo, a budget apartment or a house that fits the whole family. No matter what type of vacation rental you're looking for, you'll have plenty to select from with Vrbo. Here are a few top picks:

  • Nice and close to the heart of Bennington, "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow" is ideal for a quick break. While you're in the area, make sure you get to leading attractions like The Governor's House and Noyes House Museum.
  • Eat, sleep and explore from "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities", another enticing option. Tea at the Governor's House and Ryder Brook Golf Course should be on your itinerary when it's time to go sightseeing.

What are the best romantic weekend getaways in or near Bennington?

Nothing says "I love you" like a romantic weekend together. If you want to spend a couple of nights away with your sweetheart, we've got some romantic getaways in and around Bennington that will set your hearts aflutter:

  • Put on some love songs and chill together at "Historic Renovated Barn At Boorn Brook Farm". Around 20 miles from Bennington, this property has everything you need for a couple's weekend away, including beauty services and massage services.
  • "Charming Vermont Home On 7 Acres W" is another option that'll woo you. It's around 25 miles from Bennington and comes with winery tours and a fireplace.

Are there mansions for rent in or near Bennington?

Nothing says "Best. Vacation. Ever." like staying in a mansion. Treat your nearest and dearest to a memorable escape at one of these mansions for rent in or near Bennington:

  • Around 0.1 miles to the southwest of Bennington is "Victorian Mansion's Jim - Dandy Suite W". As well as its grand design, you'll also love its first-class amenities, such as a porch and free WiFi.
  • With a fireplace, a garden and loads of other top-rated amenities, "Lakeside Victorian Mansion With Hot Tub" will get your guests' tick of approval. This opulent home is around 17 miles to the east of Bennington.

What are the best large group vacation rentals in or near Bennington?

Big groups mean huge fun. They also mean finding someplace that'll effortlessly fit your crew. Browse our large group vacation rentals in or around Bennington and get everybody together under one roof:

  • A nice range of amenities including a kitchen and a fireplace make "True Ski In/ski Out 3 Bedroom End Unit Directly On Mount Snow" a favorite with groups. This generous getaway has 3 bedrooms and sleeps up to 12 guests. From the heart of Bennington, it's around 16 miles away to the east.
  • "Mt. Snow Area Private Estate On 100 Acres W" is another impressive option. It's around 25 miles to the east of Bennington, has 10 bedrooms and accommodates up to 21 guests. A sauna and a garden are just a couple of things designed to make your stay more comfortable.

What are the best houses for rent with a pool in or near Bennington?

A pool is often a must-have when choosing where to spend your vacation, especially if you're traveling with kids who are full of beans. Browse these houses with a pool in or near Bennington and fill your days with frolicking and fun:

  • Pack your swimsuit and take your gang to "Downtown Victorian House". There are also lots of other great amenities here, including a kitchen and free toiletries.
  • "Meme's High Mountain Lake House" is the type of place you go to leave it all behind and enjoy your surroundings, starting with its awesome pool. Childrens activities and a porch are also on hand to make your stay as comfortable as possible.

Not sure what the weather is like in Bennington? It has a humid continental climate, with average summertime temperatures ranging from 55 ºF to 75 ºF. If you're after a little more inspiration on where to stay in this impressive destination, use the search bar at the top of the page and adjust the filters to browse through our entire selection of Bennington vacation rentals.