Choose from 28 vacation rentals located in Bennington, Vermont. Top filters in Bennington include Parking, Air conditioner, and Internet / Wifi. Prices range from $91 to $500 per night. Our most popular vacation rental types near Bennington are Condo and Hotel.

Top vacation rentals in Bennington

Fall 2014
4.9
Outstanding(33 Reviews)
House
 in Bennington
Historic Home in Old Bennington, Vermont
7 guests · 3 bedrooms · 3 baths
Garden · Pool · Pets allowed

This inviting House in Bennington can fit your needs for many types of vacations, at $260 per night.

$$$$
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Front Porch
5.0
Outstanding(76 Reviews)
House
 in Bennington
Victorian Home in Bennington, Vermont
7 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Bennington at Victorian Home in Bennington, Vermont for $288 for your next trip.

$$$$
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Property view
3.7
Good(193 Reviews)
Motel
 in Bennington
Bennington Motor Inn
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Bennington for Motel, for $95 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.7
Good(327 Reviews)
Motel
 in Bennington
The Autumn Inn
Pets allowed · Kitchen / Kitchenette · Air conditioner

Experience the best of Bennington with this Motel available for $99. This property is equipped with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Vacation rentals with parking in Bennington

Property view
3.4
Average(84 Reviews)
Motel
 in Bennington
Starlight Inn
Garden · Pets allowed · Kitchen / Kitchenette

Looking for the perfect place to call home during your trip to Bennington? This Motel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Property view
4.7
Outstanding(71 Reviews)
Inn
 in Bennington
Four Chimneys Inn
Garden · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Bennington at Four Chimneys Inn for $259 for your next trip.

$$$$
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Antique brass for full bed for peaceful nights sleep.
5.0
Outstanding(5 Reviews)
Condo
 in Bennington
Downtown Victorian House
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Bennington at Downtown Victorian House for $199 for your next trip.

$$$$
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Bedroom
5.0
Outstanding(5 Reviews)
Bed and Breakfast
 in Bennington
Victorian mansion's Jim-Dandy Suite
1 guest · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Bed and Breakfast for $238 in Bennington, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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city photo
Bennington

Bennington travel guide

Let us help you plan your perfect Bennington vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Bennington, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Bennington?

  • Parking
  • Air conditioner
  • Internet / Wifi

What are the must-visit tourist attractions in Bennington, VT?

Bennington, VT is a beautiful and historic city full of many must-visit tourist attractions. Some of the top attractions include:

  • Bennington Battle Monument
  • Bennington Museum
  • Old First Church
  • Roberta's Grave

Visitors can also take in the stunning natural beauty of the area by visiting Mount Anthony, the Robert Frost Stone House Museum, and the Bennington Center for the Arts.

How can I get around in Bennington, VT?

You can get around in Bennington, VT in the following ways:

  • By car
  • By bus
  • By bike

The Bennington County Transportation (BCTS) provides bus service throughout Bennington County, and there are several bike paths and trails for cycling.

Where can I find affordable accommodation in Bennington, VT?

For affordable accommodation in Bennington, VT, consider the following options:

  • The Comfort Inn Bennington: Located just minutes from downtown Bennington, this hotel offers free parking and complimentary breakfast.
  • The Hampton Inn Bennington: Located off the main highway, this hotel offers a heated indoor pool and free WiFi.
  • The Econo Lodge Bennington: This hotel offers a convenient location near downtown Bennington and free parking.
  • The Holiday Inn Express Bennington: This hotel offers a free hot breakfast and free WiFi.

What is the culture like in Bennington, VT?

Bennington, VT is known for its small-town charm and thriving culture. There is a vibrant arts scene, plenty of outdoor activities, and a supportive community. Here are 5 things you should know about the culture in Bennington:

  • The Bennington Arts Guild is an organization that promotes and fosters the arts in the area.
  • The Bennington Free Library offers a variety of resources, from books and magazines to classes and events.
  • The Bennington Museum is a great place to learn about the history of the town and the surrounding area.
  • Outdoor activities are abundant, with plenty of options for hiking, biking, and camping.
  • The town is very welcoming and the community is very supportive of one another.

Is Bennington, VT safe to travel to?

Bennington, VT is generally safe to travel to. Here are a few precautions to take when visiting:

  • Be aware of your surroundings.
  • Avoid walking alone at night.
  • Keep your valuables secure.

What are the popular shopping destinations in Bennington, VT?

Bennington, VT is known for its many shopping destinations. Here are some of the most popular:

  • Bennington Potters
  • The Bennington Bookshop
  • The Bennington Museum

Whether you're looking for pottery, books, or art, Bennington has something for everyone!

What are the best neighborhoods to visit in Bennington, VT?

The best neighborhoods to visit in Bennington, VT are:

  • Downtown Bennington
  • North Bennington
  • Old Bennington

Downtown Bennington is the main hub of the city, with plenty of shops, restaurants, and attractions. North Bennington is a charming residential area with beautiful views of the mountains. Old Bennington is home to the Bennington Battle Monument, the Bennington Museum, and the Bennington Center for the Arts.

Where is Bennington, VT?

Bennington, VT is located in the southwestern corner of the state, in the picturesque Green Mountains. It is near the states of New York, Massachusetts, and Connecticut. The town is known for its historic buildings, including the Bennington Battle Monument, and its many outdoor recreational activities, such as skiing, hiking, and cycling.

What are the most popular vacation rental amenities in Bennington, VT?

The most popular vacation rental amenities in Bennington, VT include:

  • Outdoor space, such as a patio or balcony
  • Fully-equipped kitchen
  • High-speed Wi-Fi
  • Air-conditioning
  • TV with streaming services

In addition, many vacation rentals offer extras such as private hot tubs, fireplaces, and BBQ grills.

What are the top things to do in Bennington, VT?

Bennington, VT is a great place to visit for any traveler. From outdoor activities to historical sites, there are plenty of things to do in the area. Here are some of the top activities to do in Bennington, VT:

  • Visit the Bennington Battle Monument
  • Explore the Bennington Museum
  • Hike up Mt. Anthony
  • Spend the day at the Bennington Center for the Arts

No matter what kind of activity you're looking for, Bennington, VT has something for everyone. Whether you're looking for a relaxing day of sightseeing or an adventurous outdoor experience, Bennington has it all.

What do I need to know before visiting Bennington, VT?

Before visiting Bennington, VT, it is important to know that the town is known for its scenic views, outdoor activities, and vibrant art culture. Here are some things to consider when planning a trip to this beautiful town:

  • The town is located near the border of Vermont and New York
  • The town is easily accessible from major highways and airports
  • The town is home to a variety of unique attractions, including Bennington Battle Monument, the Old First Church, and the Bennington Museum

In addition to the outdoor activities and attractions, Bennington also has a thriving culinary scene, with a variety of restaurants and cafes offering traditional New England fare, as well as internationally-inspired cuisine. There are also plenty of shopping opportunities in the town, ranging from boutique stores to larger, more well-known retail outlets.

What is the price range for rentals in Bennington?

Vacation rentals in Bennington have a price range between $91-$500. The average price for rentals in Bennington is $121 per night.

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