755+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Massachusetts
  3. Eastham

Eastham pickleball Stays, Resort Rentals, & Homes

About Eastham Vacation Rentals

Discover over 755 amazing vacation rental options in Eastham 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 Eastham.

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 1028.72 ft², with prices averaging US $548 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 Eastham.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Eastham

Type Count
Vacation Homes 573
Cottages 111
Holiday Apartments 38

Use these Quick Filters to Find a Vacation Rental in Eastham

★ 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 Eastham with PickleTrip™.

Weather in Eastham, MA

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

December - February
High 42°F       Low 21°F
March - May
High 64°F       Low 23°F
June - August
High 80°F       Low 58°F
September - November
High 75°F       Low 32°F

Top Attractions Around Eastham, MA

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


Cape Cod National Seashore
Nauset Lighthouse
Salt Pond Visitor Center
Nauset Light Beach
Eastham Windmill
Poit's Lighthouse Mini Golf
Swift-Daley House
Cooks Brook Beach
Cove Burying Ground
Arnold's Mini Golf
The Three Sisters Lighthouses
Buttonbush Trail
Schoolhouse Museum
Adventure Diving Services of Cape Cod
Edward Penniman House and Barn
Wiley Park Beach
Herring Brook Beach
First Encounter Beach
Thumpertown Beach
Campground Beach

Other Places to Stay in Eastham, MA


Cove Burying Ground 998 Properties
Edward Penniman House and Barn 973 Properties
Swift-Daley House 960 Properties
Eastham Windmill 919 Properties
First Encounter Beach 901 Properties
Wiley Park Beach 900 Properties
Herring Brook Beach 898 Properties
Adventure Diving Services of Cape Cod 875 Properties
Salt Pond Visitor Center 866 Properties
Schoolhouse Museum 862 Properties
North Eastham 220 Properties
Campground Landing 27 Properties

Frequently Asked Questions About Eastham?

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

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

Discover 16 accommodations with private or nearby pickleball courts in Eastham. Some of the best destinations to stay and play pickleball are:

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

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

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 755 properties listed in Eastham 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 755 Eastham, MA Vacation Rentals

Recently Booked Vacation Rentals in Eastham