105+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Portland pickleball Stays, Resort Rentals, & Homes

About Portland Vacation Rentals

Discover over 105 amazing vacation rental options in Portland 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 Portland.

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 903.71 ft², with prices averaging US $371 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 Portland.

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Top Pickleball-Ready Accommodation Types in Portland

Type Count
Vacation Homes 55
Holiday Apartments 18
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Portland

★ 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 Portland with PickleTrip™.

Weather in Portland, CT

View the weather forecast for Portland before booking your Portland 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 Portland, CT

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


Brownstone Exploration & Discovery Park
Arrigoni Winery
XL Center
Xfinity Theatre
University of Hartford
Toyota Presents Oakdale Theatre
Connecticut Convention Center
Quinnipiac University
Trinity College
Wesleyan University
Essex Steam Train
Lake Compounce
Connecticut Science Center
University of Connecticut-Hartford
Cabela's
Choate Rosemary Hall
Westfarms Mall
Bushnell Center for the Performing Arts
Mark Twain House
CoCo Key Water Resort Hotel & Convention Center - Waterbury

Other Places to Stay in Portland, CT


Arrigoni Winery 93 Properties
Brownstone Exploration & Discovery Park 28 Properties

Frequently Asked Questions About Portland?

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

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

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

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 105 properties listed in Portland 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 105 Portland, CT Vacation Rentals

Recently Booked Vacation Rentals in Portland