Middletown pickleball Stays, Resort Rentals, & Homes
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Luxury Places to Stay in Middletown
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Top-Rated Villas with a Pool in Middletown
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Pet-Friendly Villas in Middletown
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Large Private Villas in Middletown
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Wheelchair Accessible Holiday Homes in Middletown
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Middletown Villas, Airbnb and Holiday Homes Under $200
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Instantly Bookable Villa Rentals in Middletown
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Book a Last Minute Place to Stay in Middletown
About Middletown Vacation Rentals
Discover over 42 amazing vacation rental options in Middletown 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 Middletown.
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 1052.36 ft², with prices averaging US $225 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 Middletown.
Top Pickleball-Ready Accommodation Types in Middletown
| Type | Count |
|---|---|
| Vacation Homes | 28 |
| Holiday Apartments | 3 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Middletown
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★ 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 Middletown with PickleTrip™.
Weather in Middletown, MD
View the weather forecast for Middletown before booking your Middletown Vacation Rentals to confirm your best time to go.
Top Attractions Around Middletown, MD
PickleTrip offers a large selection of top attractions around Middletown . Research things to do on your vacation before you visit Middletown.
Other Places to Stay in Middletown, MD
Frequently Asked Questions About Middletown?
What are the top vacation rentals, resorts, and hotels in Middletown 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 Middletown. 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 Middletown!
- Charming "Cream of the Crop" Cape ~❤️of Middletown
- Countryside Cabin with Mountain Views near Surreybrooke Gardens
- Sunny And Cozy Little Lodge With A Spectacular View Of The Blue Ridge Mountains
- Luxury Cabin Nestled In The Beautiful Blue Ridge Mountains
- INDULGE - FRESH FLOWERS, MANY AMENITIES
- Historic Jefferson Farmhouse - Hike, Bike & Raft!
- Private remodeled house rent weekends, weekly, monthly. Country/Equine setting
- Enjoy the serenity of our cozy forest lodge by the Frederick Watershed
- 3-bedroom house in charming Boonsboro with WiFi, AC, and a gorgeous view!
- Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
How many PickleTrip vacation rentals or resorts are available in Middletown?
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 42 properties listed in Middletown 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.
