236+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Maryland
  3. Taylors Island

Taylors Island pickleball Stays, Resort Rentals, & Homes

About Taylors Island Vacation Rentals

Discover over 236 amazing vacation rental options in Taylors 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 Taylors 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 1780.01 ft², with prices averaging US $556 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 Taylors Island.

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Top Pickleball-Ready Accommodation Types in Taylors Island

Type Count
Vacation Homes 182
Cottages 22
Holiday Apartments 13
Villas 2

Use these Quick Filters to Find a Vacation Rental in Taylors 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 Taylors Island with PickleTrip™.

Weather in Taylors Island, MD

View the weather forecast for Taylors Island before booking your Taylors 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 Taylors Island, MD

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


Patuxent River Naval Air Station
St. Mary's College of Maryland
Calvert Cliffs State Park
Chesapeake Beach Water Park
Rod n Reel Charter Fishing
Great Marsh Park
Blackwater National Wildlife Refuge
Harriet Tubman Museum and Educational Center
Oxford Museum
St. Mary's River State Park
Historic St. Mary's City
Breezy Point Beach
Cove Point Lighthouse
Running Hare Vineyard
Harriet Tubman Underground Railroad National Historical Park
Cecil's Old Mill
Patuxent River Naval Air Museum
Long Wharf Park
Sotterley Plantation
Bay Country Shop

Frequently Asked Questions About Taylors Island?

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

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

Discover 27 accommodations with private or nearby pickleball courts in Taylors Island. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Taylors 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 Taylors 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 236 properties listed in Taylors 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.


People Also Ask

There are 236 Taylors Island, MD Vacation Rentals

Recently Booked Vacation Rentals in Taylors Island