623+ Vacation Rentals & Holiday Homes in Bennington |
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Bennington Accommodations - Hotels & Rentals

About Bennington Vacation Rentals

Discover More than 623 Incredible Getaway Rentals Available in Bennington. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Bennington.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Bennington, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Bennington. The Average Size of Places to Stay Near Bennington is 1196.57 ft², with Prices Averaging US $498 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Bennington. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Bennington

Type Count
Vacation Homes 356
Holiday Apartments 71
Cottages 25
Villas 1

Use these Quick Filters to Find a Vacation Rental in Bennington

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Bennington with Online Reservations.

Weather in Bennington, VT

View the weather forecast for Bennington before booking your Bennington Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities BenningtonGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World BenningtonGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Mount Equinox
Orvis Fly Fishing
Bennington Battle Monument
Battenkill River
Sugar Shack
Southern Vermont College
Equinox Preservation Trust
Bennington College
Lake Shaftsbury State Park
Hildene
Bennington Center for the Arts
Dana L. Thompson Memorial Park
Park McCullough House
Golf Club at Equinox
Prospect Mountain Cross-Country Ski Center
Stratton Mountain Golf Course
Bennington Museum
Dorset Playhouse
Museum of Creative Process
Lye Brook Falls

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Manchester 233 Properties
Peru 151 Properties
Manchester Center 137 Properties
Sandgate 84 Properties
Sunderland 61 Properties
Shaftsbury 57 Properties
Arlington 52 Properties
Woodford 44 Properties
Dorset 36 Properties
East Dorset 33 Properties
Winhall 32 Properties
Bondville 26 Properties

Frequently Asked Questions About Bennington?

What are the top hotels, lake houses & vacation rentals in Bennington?

We provide an array of great vacation destinations in Bennington. If you are looking to stay in or around the Bennington area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Bennington:

How many Hotels & Vacation Rentals have private pools in Bennington?

We have 15 Hotels & Vacation Rentals featuring a private pool in and near Bennington. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Bennington is best for families?

Searching for a family-friendly getaway in Bennington? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Bennington?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 623 in the Bennington area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Bennington.

Nearby Neighborhood (2) 
Neighborhood Property Count
Bromley Mountain Vacation Rentals in Bennington, Vermont 34
Forest Farms Vacation Rentals in Bennington, Vermont 455

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