443+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Rhode Island
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  4. Middletown

Middletown pickleball Stays, Resort Rentals, & Homes

About Middletown Vacation Rentals

Discover over 443 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 1031.65 ft², with prices averaging US $686 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.

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Top Pickleball-Ready Accommodation Types in Middletown

Type Count
Vacation Homes 290
Cottages 41
Holiday Apartments 37

Use these Quick Filters to Find a Vacation Rental in Middletown

★ 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, RI

View the weather forecast for Middletown before booking your Middletown 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 Middletown, RI

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


Second Beach
Newport Vineyards
Sachuest Point National Wildlife Refuge
Third Beach
Norman Bird Sanctuary
Greenvale Vineyards
Boyd's Wind Grist Mill
Atlantic Beach
Easton Point
Newport National Golf Club
Navy Beach
Whitehall Museum House
The Breakers
Newport Mansions
University of Rhode Island
Easton's Beach
Narragansett Beach
Thames Street
Fort Adams State Park
Scarborough Beach

Other Places to Stay in Middletown, RI


Newport County 1,920 Properties
Paradise Valley 1,407 Properties
Atlantic Beach 1,407 Properties
Boyd's Wind Grist Mill 1,385 Properties
Whitehall Museum House 1,113 Properties
Second Beach 1,105 Properties
Newport Vineyards 535 Properties
Norman Bird Sanctuary 516 Properties
Newport National Golf Club 448 Properties
Newport East 405 Properties
Easton's Point 55 Properties
Easton Point 55 Properties

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!

How many pickleball-ready properties have private pools in Middletown?

Discover 10 accommodations with private or nearby pickleball courts in Middletown. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Middletown? 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 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 443 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.

Nearby Neighborhood (3) 
Neighborhood Property Count
Easton's Point Vacation Rentals in Newport, Rhode Island 55
Melville Vacation Rentals in Newport, Rhode Island 61
Paradise Valley Vacation Rentals in Newport, Rhode Island 1407

People Also Ask

There are 443 Middletown, RI Vacation Rentals

Recently Booked Vacation Rentals in Middletown