600+ Private Villas and Holiday Rentals in Bennington |
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Bennington Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Bennington

Discover more than 600 vacation rentals available in Bennington. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Bennington.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Bennington, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Bennington. On average, places to stay near Bennington offer 1218.72 ft², with nightly prices averaging US $477.

With Casai, finding and comparing holiday rentals in Bennington is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Bennington

Type Count
Vacation Homes 351
Holiday Apartments 71
Cottages 23
Villas 1

Use these Quick Filters to Find a Holiday Rental in Bennington

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Bennington.

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

Top Attractions Around Bennington, VT

Casai offers a large selection of top attractions around Bennington . Research things to do on your vacation before you visit Bennington.


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

Other Places to Stay in Bennington, VT


Manchester 226 Properties
Peru 151 Properties
Manchester Center 133 Properties
Sandgate 84 Properties
Sunderland 61 Properties
Shaftsbury 57 Properties
Arlington 51 Properties
Woodford 44 Properties
Winhall 37 Properties
Dorset 35 Properties
East Dorset 33 Properties
Bondville 30 Properties

Frequently Asked Questions About Bennington?

What are the top holiday rentals in Bennington?

With numerous options available in Bennington, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Bennington:

How many holiday rentals have private pools in Bennington?

Discover a selection of holiday rentals with private pools near Bennington with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Bennington are best for families?

If you're searching for a family-friendly holiday home in Bennington, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Bennington:

How many Casai.com holiday rentals are available in Bennington?

As of 2025, Casai boasts over 600 properties listed in the Bennington area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Bennington.

Nearby Neighborhood (2) 
Neighborhood Property Count
Bromley Mountain Vacation Rentals in Bennington, Vermont 33
Forest Farms Vacation Rentals in Bennington, Vermont 455

People Also Ask

There are 600 Bennington, VT Holiday Rentals

Recently Booked Holiday Rentals in Bennington