Gillespie pickleball Stays, Resort Rentals, & Homes
About Gillespie Vacation Rentals
Discover over 44 amazing vacation rental options in Gillespie 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 Gillespie.
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 459.82 ft², with prices averaging US $143 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 Gillespie.
Top Pickleball-Ready Accommodation Types in Gillespie
| Type | Count |
|---|---|
| Vacation Homes | 21 |
| Holiday Apartments | 5 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in Gillespie
★ 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 Gillespie with PickleTrip™.
Weather in Gillespie, IL
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Top Attractions Around Gillespie, IL
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Frequently Asked Questions About Gillespie?
What are the top vacation rentals, resorts, and hotels in Gillespie 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 Gillespie. 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 Gillespie!
- Country getaway at The Campground House.
- Edwards House; Litchfield, IL; Pets welcome
- Our Little House In Litchfield
- The Carlinville Cottage
- Harrison House; Litchfield, IL; Pets welcome
- Cozy studio located in small town America, Bunker Hill, IL.
- State Street House; 3-br house; PETS WELCOME; Litchfield
- Grand Victorian Carlinville home on Rt. 66.
- Light Filled Loft on Town Square
- A small town hidden gem. You feel like a kid again when you enter the HiDeAwAy.
How many PickleTrip vacation rentals or resorts are available in Gillespie?
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 44 properties listed in Gillespie 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.
