1038+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. Canada
  2. Manitoba
  3. Winnipeg

Winnipeg pickleball Stays, Resort Rentals, & Homes

About Winnipeg Vacation Rentals

Discover over 1038 amazing vacation rental options in Winnipeg 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 Winnipeg.

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 552.55 ft², with prices averaging US $144 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 Winnipeg.

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Top Pickleball-Ready Accommodation Types in Winnipeg

Type Count
Vacation Homes 502
Holiday Apartments 262
Villas 4

Use these Quick Filters to Find a Vacation Rental in Winnipeg

★ 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 Winnipeg with PickleTrip™.

Weather in Winnipeg, MB

View the weather forecast for Winnipeg before booking your Winnipeg Vacation Rentals to confirm your best time to go.

December - February
High 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Top Attractions Around Winnipeg, MB

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


Bell MTS Place
Polo Park
University of Manitoba
RBC Convention Centre Winnipeg
Health Sciences Centre
St. Boniface Hospital
Assiniboine Park Zoo
Forks Market
University of Winnipeg
Outlet Collection Winnipeg
Club Regent Casino
Canadian Museum for Human Rights
McPhillips Station Casino
Red River College
St. Vital Centre
Burton Cummings Theatre
Victoria General Hospital
Royal Winnipeg Ballet
Celebrations Dinner Theatre
Assiniboine Park

Other Places to Stay in Winnipeg, MB


Division No. 11 679 Properties
Fort Gary 474 Properties
Tuxedo 299 Properties
St. Vital 136 Properties
Regent 128 Properties
Downtown Winnipeg 59 Properties
Exchange District 47 Properties
Headingley 45 Properties
East Kildonan 36 Properties
Steinbach 33 Properties
St. James 27 Properties
Transcona 27 Properties

Frequently Asked Questions About Winnipeg?

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

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

Discover 40 accommodations with private or nearby pickleball courts in Winnipeg. Some of the best destinations to stay and play pickleball are:

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

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

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 1038 properties listed in Winnipeg in 2025, 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 (7) 
Neighborhood Property Count
Fort Gary Vacation Rentals in Winnipeg, Manitoba 474
Downtown Winnipeg Vacation Rentals in Winnipeg, Manitoba 59
St. James Vacation Rentals in Winnipeg, Manitoba 27
Exchange District Vacation Rentals in Winnipeg, Manitoba 47
Regent Vacation Rentals in Winnipeg, Manitoba 128
West St. Paul Vacation Rentals in Winnipeg, Manitoba 26
Legislature Vacation Rentals in Winnipeg, Manitoba 602

People Also Ask

There are 1038 Winnipeg, MB Vacation Rentals

Recently Booked Vacation Rentals in Winnipeg