3507+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Cumberland pickleball Stays, Resort Rentals, & Homes

About Cumberland Vacation Rentals

Discover over 3507 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 2189.11 ft², with prices averaging US $539 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 2934
Holiday Apartments 92
Cottages 42
Villas 8

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, MD

View the weather forecast for Cumberland before booking your Cumberland 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 Cumberland, MD

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


Deep Creek Lake
Deep Creek Lake State Park
Wisp Resort
Rocky Gap State Park
Rocky Gap Casino and Golf Course
Frostburg State University
Noah's Ark
Downtown Cumberland Historic District
Rocky Gap Golf Resort
Western Maryland Railroad Station
Swallow Falls State Park
New Germany State Park
LaVale Library
Allegeny College of Maryland
Frostburg Library
Funland
F. Brooke Whiting House and Museum
Palace Theater
La Vale Tollgate House
Dan's Mountain State Park

Other Places to Stay in Cumberland, MD


Garrett County 2,658 Properties
McHenry 1,210 Properties
Oakland 919 Properties
Thayerville 648 Properties
Swanton 482 Properties
Mountain Lake Park 219 Properties
Waterfront Greens 99 Properties
Mountainside 83 Properties
Allegany County 67 Properties
Blakeslee 52 Properties
Deep Creek Lake 50 Properties
North Glade Hills 50 Properties

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 166 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 3507 properties listed in Cumberland in 2026, 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 (12) 
Neighborhood Property Count
Waterfront Greens Vacation Rentals in Cumberland, Maryland 99
Mountainside Vacation Rentals in Cumberland, Maryland 83
Blakeslee Vacation Rentals in Cumberland, Maryland 52
North Glade Hills Vacation Rentals in Cumberland, Maryland 50
Sky Valley Vacation Rentals in Cumberland, Maryland 36
Paradise Point Vacation Rentals in Cumberland, Maryland 35
Sunplace Vacation Rentals in Cumberland, Maryland 1930
Silver Ridge Vacation Rentals in Cumberland, Maryland 1893
Penelacres Vacation Rentals in Cumberland, Maryland 2186
The View Vacation Rentals in Cumberland, Maryland 1732
Turkey Neck Vacation Rentals in Cumberland, Maryland 1093
Timbers on the Yough Vacation Rentals in Cumberland, Maryland 139

People Also Ask

There are 3507 Cumberland, MD Vacation Rentals

Recently Booked Vacation Rentals in Cumberland