86+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Owls Head

Owls Head pickleball Stays, Resort Rentals, & Homes

About Owls Head Vacation Rentals

Discover over 86 amazing vacation rental options in Owls Head 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 Owls Head.

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 656.68 ft², with prices averaging US $322 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 Owls Head.

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Top Pickleball-Ready Accommodation Types in Owls Head

Type Count
Vacation Homes 34
Cottages 9
Holiday Apartments 2

Use these Quick Filters to Find a Vacation Rental in Owls Head

★ 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 Owls Head with PickleTrip™.

Weather in Owls Head, NY

View the weather forecast for Owls Head before booking your Owls Head Vacation Rentals to confirm your best time to go.

December - February
High 37°F       Low 10°F
March - May
High 64°F       Low 16°F
June - August
High 80°F       Low 54°F
September - November
High 76°F       Low 27°F

Top Attractions Around Owls Head, NY

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


Mountain View Lake
Whiteface Mountain
Titus Mountain Family Ski Center
Malone Golf Club
Santa's Workshop
Paul Smith's College Visitor Interpretive Center
Fern Lake
River Stone Wellness
Wilmington Town Beach
Wilder Homestead
Chazy Lake
Upper Chateaugay Lake
Franklin County Visitors Bureau
Malone Memorial Recreation Park
Lower Chateaugay Lake
Lake Titus
Azure Mountain Trailhead
Larry Ryan Mountain

Other Places to Stay in Owls Head, NY


Mountain View Lake 73 Properties
Town of Bellmont 29 Properties
Mountain View 26 Properties

Frequently Asked Questions About Owls Head?

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

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

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

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 86 properties listed in Owls Head 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.


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There are 86 Owls Head, NY Vacation Rentals

Recently Booked Vacation Rentals in Owls Head