8549+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Oregon
  3. Bend

Bend pickleball Stays, Resort Rentals, & Homes

About Bend Vacation Rentals

Discover over 8549 amazing vacation rental options in Bend 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 Bend.

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 1716.44 ft², with prices averaging $394 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 Bend.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Bend

Type Count
Vacation Homes 6232
Holiday Apartments 393
Cottages 97
Villas 27

Use these Quick Filters to Find a Vacation Rental in Bend

★ 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 Bend with PickleTrip™.

Weather in Bend, OR

View the weather forecast for Bend before booking your Bend 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 Bend, OR

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


Mt. Bachelor Ski Resort
Old Mill District
Les Schwab Amphitheater
Mt Bachelor
Deschutes Brewery
Downtown Bend Business Association
Smith Rock State Park
Ochoco National Forest
Drake Park
Tower Theater
Bend Rock Gym
Deschutes National Forest
Widgi Creek Golf Club
Bend River Promenade
Tetherow Golf Club
Central Bend
Prineville Reservoir State Park
Sunriver Resort Golf Course
Crooked River Ranch Golf Course
Central Oregon Community College

Other Places to Stay in Bend, OR


Oregon 25,376 Properties
Deschutes County 5,733 Properties
Sunriver 2,683 Properties
River West 837 Properties
Sisters 474 Properties
Century West 370 Properties
Prineville 354 Properties
Black Butte Ranch 305 Properties
Broken Top 299 Properties
Deer Park 235 Properties
Oregon Water Wonderland 197 Properties
Three Rivers 197 Properties

Frequently Asked Questions About Bend?

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

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

Discover 319 accommodations with private or nearby pickleball courts in Bend. Some of the best destinations to stay and play pickleball are:

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

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

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 8549 properties listed in Bend 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
Century West Vacation Rentals in Bend, Oregon 370
Broken Top Vacation Rentals in Bend, Oregon 299
Oregon Water Wonderland Vacation Rentals in Bend, Oregon 197
Southern Crossing Vacation Rentals in Bend, Oregon 146
Orchard District Vacation Rentals in Bend, Oregon 127
Overlook Park Vacation Rentals in Bend, Oregon 124
Old Bend Vacation Rentals in Bend, Oregon 119
Larkspur Vacation Rentals in Bend, Oregon 94
Mountain View District Vacation Rentals in Bend, Oregon 55
Mountain View Vacation Rentals in Bend, Oregon 55
Old Farm District Vacation Rentals in Bend, Oregon 53
Southwest Bend Vacation Rentals in Bend, Oregon 52
Deschutes River Woods Vacation Rentals in Bend, Oregon 34
RiverWild Vacation Rentals in Bend, Oregon 33
River Terrace Vacation Rentals in Bend, Oregon 31
Awbrey Butte Vacation Rentals in Bend, Oregon 835

People Also Ask

There are 8549 Bend, OR Vacation Rentals

Recently Booked Vacation Rentals in Bend