141+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  2. Maine
  3. Portland
  4. Freeport

Freeport pickleball Stays, Resort Rentals, & Homes

About Freeport Vacation Rentals

Discover over 141 amazing vacation rental options in Freeport 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 Freeport.

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 813.54 ft², with prices averaging US $440 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 Freeport.

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Top Pickleball-Ready Accommodation Types in Freeport

Type Count
Vacation Homes 58
Holiday Apartments 20
Cottages 10
Villas 2

Use these Quick Filters to Find a Vacation Rental in Freeport

★ 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 Freeport with PickleTrip™.

Weather in Freeport, ME

View the weather forecast for Freeport before booking your Freeport 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 Freeport, ME

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


LL Bean Flagship Store
Desert of Maine
Winslow Memorial Park
Harrington House
Mast Landing Sanctuary
Freeport Historical Society
Bradbury Mountain State Park
Wolfe's Neck Farm
Wolfe's Neck Woods State Park
Theater of Awesome
Wilbur's of Maine Chocolate Confections
Acadia National Park
Maine Mall
Maine Medical Center
Higgins Beach
State Theatre
Cross Insurance Arena
Portland Head Light
Bates College
Portland Museum of Art

Other Places to Stay in Freeport, ME


Bradbury Mountain State Park 127 Properties
LL Bean Flagship Store 125 Properties
Theater of Awesome 125 Properties
Freeport Historical Society 125 Properties
Harrington House 125 Properties
Wilbur's of Maine Chocolate Confections 123 Properties
Wolfe's Neck Farm 116 Properties
Mast Landing Sanctuary 108 Properties
Wolfe's Neck State Park 102 Properties
Desert of Maine 87 Properties
Winslow Memorial Park 66 Properties

Frequently Asked Questions About Freeport?

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

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

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

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 141 properties listed in Freeport 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 (1) 
Neighborhood Property Count
Bustins Island Vacation Rentals in Portland, Maine 40

People Also Ask

There are 141 Freeport, ME Vacation Rentals

Recently Booked Vacation Rentals in Freeport