1802+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Massachusetts
  3. Dukes County

Dukes County pickleball Stays, Resort Rentals, & Homes

About Dukes County Vacation Rentals

Discover over 1802 amazing vacation rental options in Dukes 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 Dukes 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 1141.14 ft², with prices averaging US $1,068 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 Dukes County.

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Top Pickleball-Ready Accommodation Types in Dukes County

Type Count
Vacation Homes 1399
Holiday Apartments 125
Cottages 121
Villas 3

Use these Quick Filters to Find a Vacation Rental in Dukes 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 Dukes County with PickleTrip™.

Weather in Dukes County, MA

View the weather forecast for Dukes County before booking your Dukes 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 Dukes County, MA

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


Oak Bluffs Harbor
Inkwell Beach
Katama Beach
Edgartown Lighthouse
Oak Bluffs Town Beach
Martha's Vineyard Film Center
South Beach
Martha's Vineyard Museum
Martha's Vineyard Chamber of Commerce
Flying Horses Carousel
Lighthouse Beach
Island Cove Miniature Golf
Gus Ben David's World of Reptiles and Birds Park
Martha's Vineyard Preservation Trust Historic Buildings
Chilmark Chocolates
Vineyard Haven Public Library
Manuel F Correlus State Forest
Gay Head Lighthouse
Aquinnah Cliffs
Island Cove Adventures
Polly Hill Arboretum
Wasque Beach
Chappaquiddick
East Chop Light
Edgartown Public Library
Lucy Vincent Beach
Trinity Park Tabernacle
Ocean Park
Long Point Beach
The Yard

Other Places to Stay in Dukes County, MA


Martha's Vineyard 1,105 Properties
Edgartown 394 Properties
Oak Bluffs 350 Properties
Vineyard Haven 253 Properties
Tisbury 160 Properties
Katama 141 Properties
Lake Tashmoo 132 Properties
West Tisbury 93 Properties
Chilmark 79 Properties
Lagoon Heights 75 Properties
East Chop 61 Properties
Aquinnah 29 Properties

Frequently Asked Questions About Dukes County?

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

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

Discover 117 accommodations with private or nearby pickleball courts in Dukes County. Some of the best destinations to stay and play pickleball are:

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

Looking for a fun and active getaway with pickleball courts in Dukes 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 Dukes 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 1802 properties listed in Dukes County 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.


People Also Ask

There are 1802 Dukes County, MA Vacation Rentals

Recently Booked Vacation Rentals in Dukes County