220+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Delaware
  3. Rehoboth Beach
  4. Fenwick Island

Fenwick Island pickleball Stays, Resort Rentals, & Homes

About Fenwick Island Vacation Rentals

Discover over 220 amazing vacation rental options in Fenwick Island 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 Fenwick Island.

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 905.31 ft², with prices averaging US $596 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 Fenwick Island.

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Top Pickleball-Ready Accommodation Types in Fenwick Island

Type Count
Vacation Homes 158
Holiday Apartments 6
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Fenwick Island

★ 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 Fenwick Island with PickleTrip™.

Weather in Fenwick Island, DE

View the weather forecast for Fenwick Island before booking your Fenwick Island 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 Fenwick Island, DE

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


Fenwick Island Lighthouse
Fenwick Island Beach
Thunder Lagoon Waterpark
DiscoverSea Shipwreck Museum
Action Watercraft
Ocean City Boardwalk
Ocean City Beach
Rehoboth Beach Boardwalk
Jolly Roger Amusement Park
Maryland Beach
Bethany Beach Boardwalk
Casino at Ocean Downs
Roland E. Powell Convention Center
Tanger Outlets
Jolly Roger at the Pier
Assateague State Park
Funland
Carousel Ice Skating Rink
Trimper's Rides
Tanger Outlet Mall

Other Places to Stay in Fenwick Island, DE


Action Watercraft 6,057 Properties
Fenwick Island Lighthouse 5,796 Properties
Thunder Lagoon Waterpark 5,691 Properties
DiscoverSea Shipwreck Museum 4,951 Properties
Fenwick Island State Park 2,768 Properties
Fenwick Island Beach 2,743 Properties
Maison Sur-Mer 2,392 Properties

Frequently Asked Questions About Fenwick Island?

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

How many pickleball-ready properties have private pools in Fenwick Island?

Discover 8 accommodations with private or nearby pickleball courts in Fenwick Island. Some of the best destinations to stay and play pickleball are:

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

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

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 220 properties listed in Fenwick Island 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.

Nearby Neighborhood (2) 
Neighborhood Property Count
Fenwick Landing Vacation Rentals in Rehoboth Beach, Delaware 5932
Maison Sur-Mer Vacation Rentals in Rehoboth Beach, Delaware 2392

People Also Ask

There are 220 Fenwick Island, DE Vacation Rentals

Recently Booked Vacation Rentals in Fenwick Island