761+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Galena pickleball Stays, Resort Rentals, & Homes

About Galena Vacation Rentals

Discover over 761 amazing vacation rental options in Galena 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 Galena.

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 1358.68 ft², with prices averaging US $393 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 Galena.

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Top Pickleball-Ready Accommodation Types in Galena

Type Count
Vacation Homes 505
Holiday Apartments 63
Villas 22
Cottages 11

Use these Quick Filters to Find a Vacation Rental in Galena

★ 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 Galena with PickleTrip™.

Weather in Galena, IL

View the weather forecast for Galena before booking your Galena 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 Galena, IL

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


Chestnut Mountain Resort
Eagle Ridge Resort
Galena Historic District
Apple River Canyon State Park
Grant Home
Washburne House Historic Site
Belvedere Mansion
SplashLand Family Water Park
Horseshoe Mound
Old Market House
Grant Park
Apple River Fort
Casper Bluff Land and Water Reserve
Dowling House
Old Blacksmith Shop
J Dubuque Monument
Apple Canyon Lake
Massbach Ridge Winery
The General at Eagle Ridge
Galena-Jo Daviess County History Museum

Other Places to Stay in Galena, IL


Casper Bluff Land and Water Reserve 672 Properties
Elizabeth 650 Properties
Jo Daviess County 645 Properties
Guilford 366 Properties
The Galena Territory 365 Properties
East Dubuque 150 Properties
West Galena 147 Properties
Stockton 70 Properties
Apple Canyon Lake 31 Properties
Lena 27 Properties
Thompson 24 Properties
Apple River 24 Properties

Frequently Asked Questions About Galena?

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

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

Discover 48 accommodations with private or nearby pickleball courts in Galena. Some of the best destinations to stay and play pickleball are:

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

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

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 761 properties listed in Galena 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
The Galena Territory Vacation Rentals in Galena, Illinois 365

People Also Ask

There are 761 Galena, IL Vacation Rentals

Recently Booked Vacation Rentals in Galena