59+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Vermont
  3. Bennington
  4. Old Bennington

Old Bennington pickleball Stays, Resort Rentals, & Homes

About Old Bennington Vacation Rentals

Discover over 59 amazing vacation rental options in Old Bennington with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Old Bennington.

Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 546.78 ft², with prices averaging US $214 per night.

With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Old Bennington.

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Top Pickleball-Ready Accommodation Types in Old Bennington

Type Count
Vacation Homes 20
Holiday Apartments 13
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Old Bennington

★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Old Bennington with PickleTrip™.

Weather in Old Bennington, VT

View the weather forecast for Old Bennington before booking your Old 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 Old Bennington, VT

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


Bennington Battle Monument
Bennington Museum
Old First Congregational Church
Mount Snow
Mass MoCA
Williams College
Mount Equinox
Mount Greylock
Williamstown Theatre Festival
Battenkill River
Sugar Shack
Southern Vermont College
Savoy Mountain State Forest
Topia Arts Center
Bennington College
Sterling and Francine Clark Art Institute
Willard Mountain
Lake Shaftsbury State Park
Grafton Lakes State Park
Bennington Center for the Arts

Other Places to Stay in Old Bennington, VT


Old First Congregational Church 66 Properties
Bennington Museum 66 Properties
Bennington Battle Monument 66 Properties

Frequently Asked Questions About Old Bennington?

What are the top vacation rentals, resorts, and hotels in Old Bennington with Courts?

Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Old Bennington. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Old Bennington!

Which vacation rentals, resorts, or hotels in Old Bennington is best for families looking for a pickleball-getaway?

Looking for a fun and active getaway with pickleball courts in Old Bennington? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.

How many PickleTrip vacation rentals or resorts are available in Old Bennington?

PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 59 properties listed in Old Bennington in 2025, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.


People Also Ask

There are 59 Old Bennington, VT Vacation Rentals

Recently Booked Vacation Rentals in Old Bennington