352+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Cumberland pickleball Stays, Resort Rentals, & Homes

About Cumberland Vacation Rentals

Discover over 352 amazing vacation rental options in Cumberland 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 Cumberland.

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 458.14 ft², with prices averaging US $236 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 Cumberland.

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Top Pickleball-Ready Accommodation Types in Cumberland

Type Count
Vacation Homes 149
Holiday Apartments 60
Cottages 28
Villas 4

Use these Quick Filters to Find a Vacation Rental in Cumberland

★ 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 Cumberland with PickleTrip™.

Weather in Cumberland, PE

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

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Top Attractions Around Cumberland, PE

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


Prince Edward Island National Park
University of Prince Edward Island
Confederation Centre of the Arts
Historic Charlottetown Waterfront
Charlottetown Mall
Brackley Beach
Charlottetown Port
Victoria Row
Victoria Park
Eastlink Centre
That Fun Place
The Guild
Government House of Prince Edward Island
Queen Elizabeth Hospital
Charlottetown Farmers Market
Red Shores Racetrack and Casino
St. Dunstan's Basilica
Victoria Playhouse
The Mack
Province House National Historic Site of Canada

Frequently Asked Questions About Cumberland?

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

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

Discover 5 accommodations with private or nearby pickleball courts in Cumberland. Some of the best destinations to stay and play pickleball are:

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

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

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 352 properties listed in Cumberland 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 352 Cumberland, PE Vacation Rentals

Recently Booked Vacation Rentals in Cumberland