106+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Oregon
  3. Portland
  4. Lake Oswego

Lake Oswego pickleball Stays, Resort Rentals, & Homes

About Lake Oswego Vacation Rentals

Discover over 106 amazing vacation rental options in Lake Oswego 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 Lake Oswego.

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 719.25 ft², with prices averaging US $290 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 Lake Oswego.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Lake Oswego

Type Count
Vacation Homes 68
Holiday Apartments 15
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Lake Oswego

★ 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 Lake Oswego with PickleTrip™.

Weather in Lake Oswego, OR

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Lake Oswego, OR

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


Portland Temple Visitors' Center
Lake Oswego Farmers' Market
Lakewood Center for the Arts
Oswego Lake Country Club
Bike Gallery
Arts Council of Lake Oswego
Millenium Plaza City Park
The Grotto - The National Sanctuary of Our Sorrowful Mother
Lakeside Bicycles
Marylhurst University
Willamette Shore Trolley
Moda Center
Oregon Convention Center
Oregon Zoo
Oregon Health and Science University
Veterans Memorial Coliseum
Washington Square Mall
Portland State University
Vancouver Mall
Portland Expo Center

Other Places to Stay in Lake Oswego, OR


Oak Creek 278 Properties
Mount Park 277 Properties
Walluga 250 Properties
Country Club - North Shore 240 Properties
Lake Grove 233 Properties
First Addition 228 Properties
Palisades 196 Properties
Blue Heron 195 Properties
Bryant 194 Properties
Foothills 178 Properties
Lakewood 161 Properties
Lake Forest 26 Properties

Frequently Asked Questions About Lake Oswego?

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

How many pickleball-ready properties have private pools in Lake Oswego?

Discover 2 accommodations with private or nearby pickleball courts in Lake Oswego. Some of the best destinations to stay and play pickleball are:

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

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

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 106 properties listed in Lake Oswego 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 (16) 
Neighborhood Property Count
Sherwood - Tualatin South Vacation Rentals in Portland, Oregon 39
Stafford - Tualatin Valley Vacation Rentals in Portland, Oregon 38
Lake Forest Vacation Rentals in Portland, Oregon 26
Mount Park Vacation Rentals in Portland, Oregon 277
Walluga Vacation Rentals in Portland, Oregon 250
Country Club - North Shore Vacation Rentals in Portland, Oregon 240
Oak Creek Vacation Rentals in Portland, Oregon 278
First Addition Vacation Rentals in Portland, Oregon 228
Forest Highlands Vacation Rentals in Portland, Oregon 283
Lake Grove Vacation Rentals in Portland, Oregon 233
Palisades Vacation Rentals in Portland, Oregon 196
Blue Heron Vacation Rentals in Portland, Oregon 195
Robinwood Vacation Rentals in Portland, Oregon 183
Foothills Vacation Rentals in Portland, Oregon 178
Lakewood Vacation Rentals in Portland, Oregon 161
Bryant Vacation Rentals in Portland, Oregon 194

People Also Ask

There are 106 Lake Oswego, OR Vacation Rentals

Recently Booked Vacation Rentals in Lake Oswego