115+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Maryland
  3. Somerset County

Somerset County pickleball Stays, Resort Rentals, & Homes

About Somerset County Vacation Rentals

Discover over 115 amazing vacation rental options in Somerset County 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 Somerset County.

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 953.86 ft², with prices averaging US $294 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 Somerset County.

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Top Pickleball-Ready Accommodation Types in Somerset County

Type Count
Vacation Homes 62
Cottages 12
Holiday Apartments 6
Villas 1

Use these Quick Filters to Find a Vacation Rental in Somerset County

★ 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 Somerset County with PickleTrip™.

Weather in Somerset County, MD

View the weather forecast for Somerset County before booking your Somerset County 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 Somerset County, MD

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


University of Maryland Eastern Shore
Smith Island
Tangier Island
Great Hope Golf Course
Crisfield Boat Rentals
Somers Cove Marina
J. Millard Tawes Museum
Terrapin Sand Point
Coventry Parish Ruins
McCready Health Pavilion
Chesapeake Health Care
Salisbury University
Chincoteague National Wildlife Refuge
St. Mary's College of Maryland
Wicomico Youth and Civic Center
Wallops Flight Facility
Point Lookout State Park
Salisbury Zoo
Assateague Point
Blackwater National Wildlife Refuge
Trap Pond State Park
Historic St. Mary's City
Museum of Chincoteague
Wor-Wic Community College
Centre at Salisbury
Coco's Funhouse
Poplar Hill Mansion
Bloxom Winery
Skydive Delmarva
Assateague Lighthouse

Other Places to Stay in Somerset County, MD


Westover 98 Properties
Frenchtown-Rumbly 83 Properties
Marion Station 81 Properties
Mount Vernon 60 Properties
Ewell 49 Properties
Smith Island 47 Properties
Tylerton 44 Properties
Deal Island 41 Properties
Chance 37 Properties
Crisfield 33 Properties
Janes Island State Park 31 Properties
Princess Anne 26 Properties

Frequently Asked Questions About Somerset County?

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

How many pickleball-ready properties have private pools in Somerset County?

Discover 3 accommodations with private or nearby pickleball courts in Somerset County. Some of the best destinations to stay and play pickleball are:

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

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

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 115 properties listed in Somerset County 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 115 Somerset County, MD Vacation Rentals

Recently Booked Vacation Rentals in Somerset County