90+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Virginia
  3. Oakley Landing

Oakley Landing pickleball Stays, Resort Rentals, & Homes

About Oakley Landing Vacation Rentals

Discover over 90 amazing vacation rental options in Oakley Landing 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 Oakley Landing.

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 1536.02 ft², with prices averaging US $422 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 Oakley Landing.

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Top Pickleball-Ready Accommodation Types in Oakley Landing

Type Count
Vacation Homes 71
Cottages 12
Holiday Apartments 4

Use these Quick Filters to Find a Vacation Rental in Oakley Landing

★ 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 Oakley Landing with PickleTrip™.

Weather in Oakley Landing, VA

View the weather forecast for Oakley Landing before booking your Oakley Landing 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 Oakley Landing, VA

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


Warsaw Town Park
Rappahannock Community College
White Stone Beach
Kinsale Museum
Chelsea Plantation
Good Luck Cellars
Rice's Hotel / Hughlett's Tavern
Menokin Foundation
Middlesex County Museum
Golden Eagle Golf Club
Vault Field Vineyards
The Dog and Oyster Vineyard
Belle Mount Vineyards
Morattico Waterfront Museum
Mary Ball Washington Museum and Library
Historic Christ Church
Rappahannock National Wildlife Refuge
Athena Vineyards and Winery
General's Ridge Vineyard and Winery
Hughlett Point Natural Area

Frequently Asked Questions About Oakley Landing?

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

How many pickleball-ready properties have private pools in Oakley Landing?

Discover 1 accommodations with private or nearby pickleball courts in Oakley Landing. Some of the best destinations to stay and play pickleball are:

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

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

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 90 properties listed in Oakley Landing 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 90 Oakley Landing, VA Vacation Rentals

Recently Booked Vacation Rentals in Oakley Landing