712+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Delaware
  3. Rehoboth Beach
  4. Dewey Beach

Dewey Beach pickleball Stays, Resort Rentals, & Homes

About Dewey Beach Vacation Rentals

Discover over 712 amazing vacation rental options in Dewey Beach 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 Dewey Beach.

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 1085.92 ft², with prices averaging US $607 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 Dewey Beach.

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Top Pickleball-Ready Accommodation Types in Dewey Beach

Type Count
Vacation Homes 416
Cottages 37
Holiday Apartments 29
Villas 5

Use these Quick Filters to Find a Vacation Rental in Dewey Beach

★ 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 Dewey Beach with PickleTrip™.

Weather in Dewey Beach, DE

View the weather forecast for Dewey Beach before booking your Dewey Beach 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 Dewey Beach, DE

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


Dewey Beach Parasail
Indian Beach
Baycenter for the Performing Arts
Dewey Beach
Fifer Orchards Local-Fresh Market - Dewey Beach
East of Maui
Sunset Park
John Waples Memorial Playground
Ocean City Beach
Rehoboth Beach Boardwalk
Lewes Beach
Maryland Beach
Bethany Beach Boardwalk
Sunset Beach
Tanger Outlets
Washington Street Mall
Sports at the Beach
Cape May - Lewes Ferry
Funland
Carousel Ice Skating Rink

Other Places to Stay in Dewey Beach, DE


Ann Acres 3,183 Properties
Fifer Orchards Local-Fresh Market - Dewey Beach 3,174 Properties
Seabreeze 3,165 Properties
East of Maui 3,120 Properties
Sunset Park 3,102 Properties
John Waples Memorial Playground 3,095 Properties
Dewey Beach 3,084 Properties
Baycenter for the Performing Arts 3,063 Properties
Dewey Beach Parasail 3,059 Properties
Indian Beach 2,890 Properties
Rehoboth by the Sea 126 Properties

Frequently Asked Questions About Dewey Beach?

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

How many pickleball-ready properties have private pools in Dewey Beach?

Discover 32 accommodations with private or nearby pickleball courts in Dewey Beach. Some of the best destinations to stay and play pickleball are:

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

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

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 712 properties listed in Dewey Beach in 2026, 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.

Nearby Neighborhood (4) 
Neighborhood Property Count
Rehoboth by the Sea Vacation Rentals in Rehoboth Beach, Delaware 126
Dodds Addition Vacation Rentals in Rehoboth Beach, Delaware 24
Seabreeze Vacation Rentals in Rehoboth Beach, Delaware 3165
Ann Acres Vacation Rentals in Rehoboth Beach, Delaware 3183

People Also Ask

There are 712 Dewey Beach, DE Vacation Rentals

Recently Booked Vacation Rentals in Dewey Beach