83+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Maryland
  3. Chestertown
  4. Tolchester Beach

Tolchester Beach pickleball Stays, Resort Rentals, & Homes

About Tolchester Beach Vacation Rentals

Discover over 83 amazing vacation rental options in Tolchester Beach 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 Tolchester Beach.

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 722.08 ft², with prices averaging US $368 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 Tolchester Beach.

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Top Pickleball-Ready Accommodation Types in Tolchester Beach

Type Count
Vacation Homes 62
Cottages 8
Holiday Apartments 6

Use these Quick Filters to Find a Vacation Rental in Tolchester Beach

★ 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 Tolchester Beach with PickleTrip™.

Weather in Tolchester Beach, MD

View the weather forecast for Tolchester Beach before booking your Tolchester Beach 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 Tolchester Beach, MD

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


White Marsh Mall
Chesapeake Bay Bridge
Fort McHenry
Sandy Point State Park
Washington College
Canton Waterfront Park
Queenstown Premium Outlets
Queenstown Harbor Golf Club
Bay Hills Golf Club
Druid Hill Park
Double Rock Park
Essex Marina
The Mainstay
Korean War Memorial
Wilmer Park
Eastern Neck National Wildlife Refuge
Rock Hall Harbor
Miami Beach
Natural History Society of Maryland Museum
Rolphs Wharf Marina

Frequently Asked Questions About Tolchester Beach?

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

How many pickleball-ready properties have private pools in Tolchester Beach?

Discover 1 accommodations with private or nearby pickleball courts in Tolchester Beach. Some of the best destinations to stay and play pickleball are:

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

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

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 83 properties listed in Tolchester Beach 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 83 Tolchester Beach, MD Vacation Rentals

Recently Booked Vacation Rentals in Tolchester Beach