78+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Virginia
  3. Midland

Midland pickleball Stays, Resort Rentals, & Homes

About Midland Vacation Rentals

Discover over 78 amazing vacation rental options in Midland 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 Midland.

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 1238.83 ft², with prices averaging US $366 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 Midland.

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Top Pickleball-Ready Accommodation Types in Midland

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 3
Villas 3

Use these Quick Filters to Find a Vacation Rental in Midland

★ 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 Midland with PickleTrip™.

Weather in Midland, VA

View the weather forecast for Midland before booking your Midland 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 Midland, VA

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


Marine Corps Base Quantico
Potomac Mills
Jiffy Lube Live
Central Park Fun Land
National Museum of the Marine Corps
Fredericksburg Expo and Conference Center
Manassas National Battlefield Park
FBI Academy
Splash Down Water Park
University of Mary Washington
Spotsylvania Towne Centre
Quantico National Cemetery
Manassas Museum
Chancellorsville Battlefield
The Loft
Prince William Hospital
Prince William Forest Park
G. Richard Pfitzner Stadium
Fredericksburg and Spotsylvania National Military Park
Paradise Springs Winery

Other Places to Stay in Midland, VA


Somerville 108 Properties
Casanova 71 Properties

Frequently Asked Questions About Midland?

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

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

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

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 78 properties listed in Midland 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 78 Midland, VA Vacation Rentals

Recently Booked Vacation Rentals in Midland