Chesapeake pickleball Stays, Resort Rentals, & Homes
About Chesapeake Vacation Rentals
Discover over 180 amazing vacation rental options in Chesapeake 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 Chesapeake.
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 462.82 ft², with prices averaging US $234 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 Chesapeake.
Top Pickleball-Ready Accommodation Types in Chesapeake
| Type | Count |
|---|---|
| Vacation Homes | 68 |
| Holiday Apartments | 25 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake
★ 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 Chesapeake with PickleTrip™.
Weather in Chesapeake, VA
View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.
Top Attractions Around Chesapeake, VA
PickleTrip offers a large selection of top attractions around Chesapeake . Research things to do on your vacation before you visit Chesapeake.
Other Places to Stay in Chesapeake, VA
Frequently Asked Questions About Chesapeake?
What are the top vacation rentals, resorts, and hotels in Chesapeake 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 Chesapeake. 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 Chesapeake!
- Beautiful home in Chesapeake
- Fully renovated and Modernized home in Chesapeake
- Beautiful home in Chesapeake
- Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
- Looking for 30 days or more contact me via VRBO for special pricing. Hot Tub
- The Sparks Home! Relaxing Space + Lux Kitchen
- Great Studio | Pool & Hot Tub. Your Next Vacation
- The Full House
- Beautiful 2-bedroom entire apartment central to everything!
- Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
How many pickleball-ready properties have private pools in Chesapeake?
Discover 8 accommodations with private or nearby pickleball courts in Chesapeake. Some of the best destinations to stay and play pickleball are:
- Delta Hotels by Marriott Chesapeake Norfolk
- Hampton Inn & Suites Chesapeake-Battlefield Boulevard
- SpringHill Suites Chesapeake Greenbrier
- Staybridge Suites Chesapeake-Virginia Beach by IHG
Which vacation rentals, resorts, or hotels in Chesapeake is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Chesapeake? 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.
- Private, Spacious Studio Apartment, Bathroom
- Spacious Chesapeake Home w/Pool Table!
- Hampton Inn Norfolk/Chesapeake (Greenbrier Area)
How many PickleTrip vacation rentals or resorts are available in Chesapeake?
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 180 properties listed in Chesapeake 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 (7)
| Neighborhood | Property Count |
|---|---|
| Greenbrier East Vacation Rentals in Chesapeake, Virginia | 184 |
| Greenbrier West Vacation Rentals in Chesapeake, Virginia | 66 |
| Western Branch North Vacation Rentals in Chesapeake, Virginia | 71 |
| Deep Creek South Vacation Rentals in Chesapeake, Virginia | 149 |
| Churchland Vacation Rentals in Chesapeake, Virginia | 66 |
| Great Bridge Vacation Rentals in Chesapeake, Virginia | 106 |
| Great Bridge East Vacation Rentals in Chesapeake, Virginia | 27 |
