63+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Jessup pickleball Stays, Resort Rentals, & Homes

About Jessup Vacation Rentals

Discover over 63 amazing vacation rental options in Jessup 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 Jessup.

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 500.12 ft², with prices averaging US $152 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 Jessup.

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Top Pickleball-Ready Accommodation Types in Jessup

Type Count
Vacation Homes 16
Holiday Apartments 11

Use these Quick Filters to Find a Vacation Rental in Jessup

★ 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 Jessup with PickleTrip™.

Weather in Jessup, MD

View the weather forecast for Jessup before booking your Jessup 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 Jessup, MD

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


Historic Savage Mill
TagParty RECON
National Aquarium in Baltimore
Baltimore Cruise Terminal
University of Maryland-College Park
Johns Hopkins University
Baltimore Convention Center
Johns Hopkins Hospital
Horseshoe Casino Baltimore
Smithsonian's National Zoo
Baltimore Inner Harbor Marina
Arundel Mills Mall
FedEx Field
M&T Bank Stadium
Oriole Park at Camden Yards
Maryland Live Casino
U.S. Naval Academy
Towson University
Howard University
Maryland Zoo

Other Places to Stay in Jessup, MD


Savage-Guilford 103 Properties
Historic Savage Mill 101 Properties
TagParty RECON 97 Properties

Frequently Asked Questions About Jessup?

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

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

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

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 63 properties listed in Jessup 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 63 Jessup, MD Vacation Rentals

Recently Booked Vacation Rentals in Jessup