603+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Southwest Middlesex

Southwest Middlesex pickleball Stays, Resort Rentals, & Homes

About Southwest Middlesex Vacation Rentals

Discover over 603 amazing vacation rental options in Southwest Middlesex 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 Southwest Middlesex.

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 448.93 ft², with prices averaging US $187 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 Southwest Middlesex.

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Top Pickleball-Ready Accommodation Types in Southwest Middlesex

Type Count
Vacation Homes 306
Holiday Apartments 153
Cottages 42
Villas 6

Use these Quick Filters to Find a Vacation Rental in Southwest Middlesex

★ 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 Southwest Middlesex with PickleTrip™.

Weather in Southwest Middlesex, ON

View the weather forecast for Southwest Middlesex before booking your Southwest Middlesex 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 Southwest Middlesex, ON

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


Boler Mountain Ski Resort
White Oaks Mall
Storybook Gardens
Springbank Park
London Regional Children's Museum
Bellamere Winery and Event Centre
Parkwood Hospital
Earl Nichols Arena
Adventures on Wonderland
Uncle Tom's Cabin
Port Stanley Main Beach
Elgin County Museum
Thames Valley Golf Course
Ska-Nah-Doht Village and Museum
St. Thomas-Elgin Public Art Centre
Victoria Playhouse Petrolia
Oakridge Arena
The Mary Webb Centre
Port Stanley Terminal Rail
Waterworks Park

Other Places to Stay in Southwest Middlesex, ON


Glencoe 491 Properties

Frequently Asked Questions About Southwest Middlesex?

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

How many pickleball-ready properties have private pools in Southwest Middlesex?

Discover 19 accommodations with private or nearby pickleball courts in Southwest Middlesex. Some of the best destinations to stay and play pickleball are:

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

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

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 603 properties listed in Southwest Middlesex 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.


People Also Ask

There are 603 Southwest Middlesex, ON Vacation Rentals

Recently Booked Vacation Rentals in Southwest Middlesex