Smith Park, IL pickleball Stays, Resort Rentals, & Homes
- Chicago
- ·
- Sheffield Neighbors
- 0.27 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Parking
- Balcony/Terrace
- View
- Kitchen
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
- Chicago
- ·
- Logan Square
- 1.11 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Chicago
- ·
- Wicker Park
- 0.38 mi to center
- Hot Tub
- Parking
- Balcony/Terrace
- View
- Chicago
- ·
- Near North Side
- 0.13 mi to center
- Parking
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Chicago
- ·
- River West
- 0.21 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- River West
- 0.20 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Luxury Places to Stay in Smith Park
- Chicago
- ·
- East Village
- 0.24 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- River North
- 0.20 mi to center
- Parking
- View
- Air Conditioner
- Internet
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Near North Side
- 0.30 mi to center
- Private Pool
- Parking
- Pool
- Kitchen
- Chicago
- ·
- West Lakeview
- 0.38 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
Top-Rated Villas with a Pool in Smith Park
- Chicago
- ·
- West Loop Gate
- 0.20 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.28 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.28 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.92 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.92 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.92 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
- Chicago
- ·
- Near North Side
- 0.14 mi to center
- Parking
- Pool
- Balcony/Terrace
- Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.92 mi to center
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
Pet-Friendly Villas in Smith Park
- Chicago
- ·
- Sheffield Neighbors
- 0.13 mi to center
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Chicago
- ·
- Sheffield Neighbors
- 0.18 mi to center
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
- Chicago
- ·
- Near West Side
- 0.34 mi to center
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Chicago
- ·
- Sheffield and DePaul
- 0.13 mi to center
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Chicago
- ·
- River North
- 0.12 mi to center
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
Large Private Villas in Smith Park
- Chicago
- ·
- Sheffield Neighbors
- 0.22 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Parking
- Air Conditioner
- Internet
- Child Friendly
- Parking
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- River North
- 0.64 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Chicago
- ·
- River North
- 0.78 mi to center
- Balcony/Terrace
- Air Conditioner
- Internet
- Child Friendly
- Parking
- Spa
- Balcony/Terrace
- Kitchen
- Chicago
- ·
- Killgubbin
- 0.23 mi to center
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
- Chicago
- ·
- Near North Side
- 0.36 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Chicago
- ·
- Sheffield and DePaul
- 0.21 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
Wheelchair Accessible Holiday Homes in Smith Park
- Chicago
- ·
- Near North Side
- 0.25 mi to center
- Parking
- Pool
- Kitchen
- Air Conditioner
- Chicago
- ·
- Near West Side
- 0.56 mi to center
- Parking
- Air Conditioner
- Internet
- Child Friendly
- Breakfast
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- River North
- 0.12 mi to center
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Parking
- Air Conditioner
- Internet
- Child Friendly
- Chicago
- ·
- Downtown Chicago
- 0.58 mi to center
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Chicago
- ·
- Near North Side
- 0.32 mi to center
- Parking
- Air Conditioner
- Internet
- Child Friendly
- Chicago
- ·
- Near North Side
- 0.32 mi to center
- Parking
- Air Conditioner
- Internet
- Child Friendly
- Chicago
- ·
- Near North Side
- 0.32 mi to center
- Parking
- Air Conditioner
- Internet
- Child Friendly
Smith Park Villas, Airbnb and Holiday Homes Under $200
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
- Chicago
- ·
- River West
- 0.13 mi to center
- Parking
- Air Conditioner
- Internet
- Accessibility
- Kitchen
- Air Conditioner
- Internet
- Laundry
- Parking
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- Pulaski Park
- 0.24 mi to center
- Parking
- Air Conditioner
- Internet
- Pet Friendly
- Chicago
- ·
- Logan Square
- 0.48 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- Logan Square
- 0.48 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- Logan Square
- 0.48 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- River West
- 0.33 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
Instantly Bookable Villa Rentals in Smith Park
- Chicago
- ·
- South Austin
- 0.67 mi to center
- Hot Tub
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- Sheffield and DePaul
- 0.16 mi to center
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
- Chicago
- ·
- Near West Side
- 0.15 mi to center
- Parking
- Ocean View
- View
- Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
- Chicago
- ·
- Near West Side
- 0.15 mi to center
- Parking
- Ocean View
- View
- Kitchen
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
- Chicago
- ·
- Sheffield Neighbors
- 0.18 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Chicago
- ·
- Logan Square
- 0.76 mi to center
- Parking
- Kitchen
- Air Conditioner
- Internet
- Parking
- Ocean View
- Balcony/Terrace
- View
Book a Last Minute Place to Stay in Smith Park
About Smith Park Vacation Rentals
Discover over 2932 amazing vacation rental options in Smith Park 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 Smith Park.
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 783.78 ft², with prices averaging US $366 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 Smith Park.
Top Pickleball-Ready Accommodation Types in Smith Park
| Type | Count |
|---|---|
| Holiday Apartments | 1973 |
| Vacation Homes | 424 |
| Villas | 5 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Smith Park
★ 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 Smith Park with PickleTrip™.
Weather in Smith Park, IL
View the weather forecast for Smith Park before booking your Smith Park Vacation Rentals to confirm your best time to go.
Frequently Asked Questions About Smith Park?
What are the top vacation rentals, resorts, and hotels in Smith Park 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 Smith Park. 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 Smith Park!
- Private Cozy Cottage House in Lincoln Park w/Porch
- Modern 3-Bed Stay w/Patio, Firepit, & Garage Parking Spot
- The Sono Chicago
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- 1F Chicago's Little italy Graystone nearDowntown
- Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- 4BR Old Town Chicago Loft | Walk to Wells St
How many pickleball-ready properties have private pools in Smith Park?
Discover 30 accommodations with private or nearby pickleball courts in Smith Park. Some of the best destinations to stay and play pickleball are:
- Level River North | Deluxe One-Bedroom Suite, Downtown Chicago
- Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop
- Level River North | Executive One-Bedroom Suite, Sophistication Downtown
- Level River North | Deluxe Two-Bedroom Suite, Where Everyone Gets Their Space
Which vacation rentals, resorts, or hotels in Smith Park is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Smith Park? 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.
- King Bed| Near Downtown & United Ctr+Walk to train
- The Orleans Floor 3 Private rooftop deck
- Ray's Bucktown B&B
How many PickleTrip vacation rentals or resorts are available in Smith Park?
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 2932 properties listed in Smith Park 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 (2)
| Neighborhood | Property Count |
|---|---|
| West Town Vacation Rentals in Chicago, Illinois | 318 |
| Ukrainian Village Vacation Rentals in Chicago, Illinois | 3682 |






















































