Madison pickleball Stays, Resort Rentals, & Homes
9.6
Exceptional
(12 Reviews)
- Collinsville
- East St. Louis
- 1.78 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $147/Night
For 7 Nights US $1,029
10.0
Exceptional
(13 Reviews)
1194.79 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Parking
US $162/Night
For 7 Nights US $1,134
9.4
Exceptional
(75 Reviews)
- St. Louis
- Grand Center
- 0.16 mi to center
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $196/Night
For 7 Nights US $1,374
5.2
Average
(5 Reviews)
- St. Louis
- Pontoon Beach
- 1.18 mi to center
1800 ft²
12 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $302/Night
For 7 Nights US $2,116
10.0
Exceptional
(9 Reviews)
- St. Louis
- Downtown St. Louis
- 1.30 mi to center
699.65 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $191/Night
For 7 Nights US $1,340
2.0
Average
(4 Reviews)
- St. Louis
- Pontoon Beach
- 1.53 mi to center
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $135/Night
For 7 Nights US $944
New
6 Guests
2 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $174/Night
For 7 Nights US $1,217
10.0
Exceptional
(1 Review)
- St. Louis
- Central West End
- 0.59 mi to center
565 ft²
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $178/Night
For 7 Nights US $1,244
New
16 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $819/Night
For 7 Nights US $5,736
Luxury Places to Stay in Madison
Over 1441+ Luxury Places to Stay in or Near Madison
New
10 Guests
4 Bedrooms
4 Bathrooms
House
- Pet Friendly
- Parking
- Air Conditioner
US $8,050/Night
For 7 Nights US $56,350
New
- St. Louis
- Downtown St. Louis
- 0.77 mi to center
6 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Condo
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $2,742/Night
For 7 Nights US $19,194
New
- St. Louis
- Downtown St. Louis
- 1.39 mi to center
12000 ft²
60 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $2,648/Night
For 7 Nights US $18,536
New
16 Guests
9 Bedrooms
3 Bathrooms
Apartment
- Parking
- Air Conditioner
- Internet
US $1,656/Night
For 7 Nights US $11,592
9.4
Exceptional
(8 Reviews)
- St. Louis
- Central West End
- 0.41 mi to center
34 Guests
12 Bedrooms
10 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,655/Night
For 7 Nights US $11,587
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown West
- 0.46 mi to center
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Kitchen
US $1,492/Night
For 7 Nights US $10,447
New
5198.97 ft²
30 Guests
14 Bedrooms
4 Bathrooms
House
- Hot Tub
- Parking
- Air Conditioner
US $1,366/Night
For 7 Nights US $9,562
10.0
Exceptional
(24 Reviews)
- St. Louis
- Downtown St. Louis
- 0.81 mi to center
1872 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,010/Night
For 7 Nights US $7,067
New
1700.7 ft²
15 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $971/Night
For 7 Nights US $6,794
Top-Rated Villas with a Pool in Madison
Over 101+ Top-Rated Private Villas with a Pool in or Near Madison
10.0
Exceptional
(3 Reviews)
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
1184 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $218/Night
For 7 Nights US $1,523
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
1184 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $213/Night
For 7 Nights US $1,491
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
748 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $206/Night
For 7 Nights US $1,441
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
748 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $173/Night
For 7 Nights US $1,212
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown St. Louis
- 0.52 mi to center
748 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $158/Night
For 7 Nights US $1,108
9.4
Exceptional
(3357 Reviews)
- St. Louis
- Downtown St. Louis
- 1.12 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Balcony/Terrace
US $189/Night
For 7 Nights US $1,326
9.4
Exceptional
(1349 Reviews)
- St. Louis
- Downtown St. Louis
- 0.11 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $162/Night
For 7 Nights US $1,132
9.4
Exceptional
(1002 Reviews)
- St. Louis
- Downtown St. Louis
- 1.35 mi to center
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Spa
- Fireplace/Heating
US $380/Night
For 7 Nights US $2,660
9.2
Exceptional
(92 Reviews)
- St. Louis
- Downtown St. Louis
- 1.33 mi to center
798.32 ft²
18 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Hot Tub
- Spa
US $667/Night
For 7 Nights US $4,667
Pet-Friendly Villas in Madison
Over 539+ Pet-Friendly Private Villas in or Near Madison
New
- St. Louis
- Central West End
- 0.60 mi to center
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
US $232/Night
For 7 Nights US $1,623
10.0
Exceptional
(1 Review)
1980.56 ft²
8 Guests
4 Bedrooms
3 Bathrooms
House
- Pet Friendly
- Parking
- Air Conditioner
US $755/Night
For 7 Nights US $5,288
8.4
Excellent
(130 Reviews)
- St. Louis
- Grand Center
- 0.47 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $156/Night
For 7 Nights US $1,092
9.6
Exceptional
(29 Reviews)
- Collinsville
- East St. Louis
- 1.60 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $222/Night
For 7 Nights US $1,552
10.0
Exceptional
(1 Review)
- St. Louis
- Central West End
- 0.24 mi to center
2820.14 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $560/Night
For 7 Nights US $3,921
10.0
Exceptional
(5 Reviews)
- St. Louis
- Downtown West
- 0.50 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $366/Night
For 7 Nights US $2,560
10.0
Exceptional
(3 Reviews)
- St. Louis
- Central West End
- 0.24 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $225/Night
For 7 Nights US $1,577
10.0
Exceptional
(2 Reviews)
- St. Louis
- Downtown West
- 0.46 mi to center
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $207/Night
For 7 Nights US $1,449
10.0
Exceptional
(1 Review)
- St. Louis
- Downtown West
- 0.46 mi to center
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $267/Night
For 7 Nights US $1,867
Large Private Villas in Madison
Over 210+ Large Villas in or Near Madison for Groups and Families
New
- St. Louis
- Central West End
- 0.51 mi to center
2052 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $694/Night
For 7 Nights US $4,860
10.0
Exceptional
(1 Review)
3498.27 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Villa
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $270/Night
For 7 Nights US $1,890
6.0
Good
(6 Reviews)
- St. Louis
- Downtown St. Louis
- 1.55 mi to center
1000 ft²
10 Guests
1 Bedroom
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $241/Night
For 7 Nights US $1,689
10.0
Exceptional
(1 Review)
1194.79 ft²
12 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- View
- Parking
US $242/Night
For 7 Nights US $1,694
New
10 Guests
2 Bedrooms
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $238/Night
For 7 Nights US $1,663
8.8
Fabulous
(9 Reviews)
- St. Louis
- Downtown St. Louis
- 1.40 mi to center
2000 ft²
20 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $389/Night
For 7 Nights US $2,726
10.0
Exceptional
(22 Reviews)
- St. Louis
- Near Southside
- 0.27 mi to center
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $394/Night
For 7 Nights US $2,761
10.0
Exceptional
(14 Reviews)
5000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $704/Night
For 7 Nights US $4,926
10.0
Exceptional
(8 Reviews)
- St. Louis
- Central West End
- 0.16 mi to center
12 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $363/Night
For 7 Nights US $2,541
Wheelchair Accessible Holiday Homes in Madison
Over 483+ Wheelchair Accessible Villas and Holiday Homes in or Near Madison
New
- St. Louis
- Downtown St. Louis
- 0.79 mi to center
1200 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $318/Night
For 7 Nights US $2,225
9.3
Exceptional
(6 Reviews)
- St. Louis
- Downtown St. Louis
- 1.32 mi to center
645.83 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
US $214/Night
For 7 Nights US $1,495
8.0
Excellent
(55 Reviews)
- St. Louis
- Central West End
- 0.79 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Breakfast
- Kitchen
- Parking
US $200/Night
For 7 Nights US $1,400
New
- St. Louis
- Downtown St. Louis
- 0.83 mi to center
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $257/Night
For 7 Nights US $1,798
9.0
Exceptional
(8 Reviews)
1485.42 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
US $176/Night
For 7 Nights US $1,232
10.0
Exceptional
(8 Reviews)
- St. Louis
- Downtown St. Louis
- 0.65 mi to center
2000 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $333/Night
For 7 Nights US $2,334
10.0
Exceptional
(4 Reviews)
- St. Louis
- Downtown St. Louis
- 1.28 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $439/Night
For 7 Nights US $3,073
10.0
Exceptional
(3 Reviews)
- St. Louis
- Downtown West
- 0.50 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $176/Night
For 7 Nights US $1,231
10.0
Exceptional
(2 Reviews)
- St. Louis
- Central West End
- 0.26 mi to center
675 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $148/Night
For 7 Nights US $1,037
Madison Villas, Airbnb and Holiday Homes Under $200
Over 856+ Madison Private Villas, Airbnb and Holiday Homes Under $200
New
- St. Louis
- Downtown St. Louis
- 1.21 mi to center
8 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Air Conditioner
- Child Friendly
US $159/Night
For 7 Nights US $1,116
10.0
Exceptional
(3 Reviews)
721.18 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Child Friendly
- Security/Safety
US $86/Night
For 7 Nights US $603
New
- St. Louis
- Central West End
- 0.44 mi to center
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $152/Night
For 7 Nights US $1,067
New
- St. Louis
- Downtown St. Louis
- 1.06 mi to center
947 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $149/Night
For 7 Nights US $1,043
10.0
Exceptional
(1 Review)
1194.79 ft²
4 Guests
1 Bedroom
2 Bathrooms
Apartment
- Parking
- Air Conditioner
- Internet
US $103/Night
For 7 Nights US $724
New
- St. Louis
- Downtown St. Louis
- 0.69 mi to center
614 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $70/Night
For 7 Nights US $490
10.0
Exceptional
(49 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $146/Night
For 7 Nights US $1,023
10.0
Exceptional
(47 Reviews)
800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $90/Night
For 7 Nights US $630
10.0
Exceptional
(46 Reviews)
1200 ft²
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $154/Night
For 7 Nights US $1,075
Instantly Bookable Villa Rentals in Madison
Over 681+ Instantly Bookable Private Villas in or Near Madison
New
1500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $255/Night
For 7 Nights US $1,782
10.0
Exceptional
(4 Reviews)
- St. Louis
- Downtown St. Louis
- 0.68 mi to center
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $304/Night
For 7 Nights US $2,128
New
- St. Louis
- Granite City
- 3.23 mi to center
8 Guests
3 Bedrooms
1 Bathroom
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $210/Night
For 7 Nights US $1,473
10.0
Exceptional
(53 Reviews)
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $229/Night
For 7 Nights US $1,603
10.0
Exceptional
(17 Reviews)
- St. Louis
- Downtown St. Louis
- 1.26 mi to center
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $262/Night
For 7 Nights US $1,831
10.0
Exceptional
(17 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $193/Night
For 7 Nights US $1,350
10.0
Exceptional
(9 Reviews)
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $180/Night
For 7 Nights US $1,258
10.0
Exceptional
(6 Reviews)
2200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $264/Night
For 7 Nights US $1,846
10.0
Exceptional
(2 Reviews)
- St. Louis
- Lafayette Square
- 0.17 mi to center
1800 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $212/Night
For 7 Nights US $1,487
Book a Last Minute Place to Stay in Madison
About Madison Vacation Rentals
Discover over 1450 amazing vacation rental options in Madison 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 Madison.
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 749.13 ft², with prices averaging US $1,177 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 Madison.
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Top Pickleball-Ready Accommodation Types in Madison
| Type | Count |
|---|---|
| Holiday Apartments | 893 |
| Vacation Homes | 358 |
| Cottages | 3 |
| Villas | 2 |
Use these Quick Filters to Find a Vacation Rental in Madison
★ 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 Madison with PickleTrip™.
Weather in Madison, IL
View the weather forecast for Madison before booking your Madison Vacation Rentals to confirm your best time to go.
December - February
High 44°F Low 15°F
March - May
High 68°F Low 26°F
June - August
High 82°F Low 57°F
September - November
High 79°F Low 27°F
Top Attractions Around Madison, IL
PickleTrip offers a large selection of top attractions around Madison . Research things to do on your vacation before you visit Madison.
Frequently Asked Questions About Madison?
What are the top vacation rentals, resorts, and hotels in Madison 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 Madison. 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 Madison!
- World’s Fair Charm -Two Story 3 bdrm
- Classy Midtown 3BR, King Master
- Historic Soulard King 2BR Apt w/Private Deck
- The Dackel - Townhouse in Historic Soulard
- NEW! Luxurious Soulard Townhome w/Brewery Views!
- Luxury Corporate Loft Suites In Soulard
- Luxury Brownstones in Historic Soulard
- Centrally Located Home Perfect for Family Getaway
- The Luck Dragon Loft
- Spacious 4-bedroom townhome in St. Louis
How many pickleball-ready properties have private pools in Madison?
Discover 13 accommodations with private or nearby pickleball courts in Madison. Some of the best destinations to stay and play pickleball are:
- Incredible 2 story city penthouse with rooftop pool, hot tub & views!
- Drury Plaza St. Louis at the Arch
- Perfectly Appointed Suite for Groups! Free Wi-Fi!
- Drury Inn and Suites St Louis Union Station
Which vacation rentals, resorts, or hotels in Madison is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Madison? 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.
- Charming Lafayette Square Home - Walk to Park/Restaurants - Downtown STL
- Brick & Bed Riverfront Lofts, G 208
- Hidden Gem | JZ Vacation Rentals
How many PickleTrip vacation rentals or resorts are available in Madison?
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 1450 properties listed in Madison 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.
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