1213+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Temperanceville
  4. Assawoman

Assawoman pickleball Stays, Resort Rentals, & Homes

About Assawoman Vacation Rentals

Discover over 1213 amazing vacation rental options in Assawoman 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 Assawoman.

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 361.01 ft², with prices averaging US $294 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 Assawoman.

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Top Pickleball-Ready Accommodation Types in Assawoman

Type Count
Vacation Homes 975
Cottages 61
Holiday Apartments 45
Villas 15

Use these Quick Filters to Find a Vacation Rental in Assawoman

★ 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 Assawoman with PickleTrip™.

Weather in Assawoman, VA

View the weather forecast for Assawoman before booking your Assawoman 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 Assawoman, VA

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


Chincoteague National Wildlife Refuge
Wallops Flight Facility
Assateague Point
Museum of Chincoteague
Bloxom Winery
Assateague Lighthouse
Eastern Shore Railway Museum
Pocomoke River State Park
Cypress Park
Delmarva Discovery Center
Oyster Bay
North Street Playhouse
Kegotank Bay
Hang Glide Virginia
SouthEast Expeditions
Robert N. Reed Downtown Waterfront Park
Coventry Parish Ruins
North Street Market
Red Queen Gallery
Captain Timothy Hill House

Frequently Asked Questions About Assawoman?

What are the top vacation rentals, resorts, and hotels in Assawoman 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 Assawoman. 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 Assawoman!

How many pickleball-ready properties have private pools in Assawoman?

Discover 35 accommodations with private or nearby pickleball courts in Assawoman. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Assawoman? 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 Assawoman?

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 1213 properties listed in Assawoman 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 1213 Assawoman, VA Vacation Rentals

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