54+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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  3. Roosevelt County

Roosevelt County pickleball Stays, Resort Rentals, & Homes

About Roosevelt County Vacation Rentals

Discover over 54 amazing vacation rental options in Roosevelt County 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 Roosevelt County.

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 303.3 ft², with prices averaging US $143 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 Roosevelt County.

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Top Pickleball-Ready Accommodation Types in Roosevelt County

Type Count
Vacation Homes 20
Cottages 2
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Roosevelt County

★ 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 Roosevelt County with PickleTrip™.

Weather in Roosevelt County, MT

View the weather forecast for Roosevelt County before booking your Roosevelt County 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 Roosevelt County, MT

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


Montana Cowboy Hall of Fame
Nellie’s Park
Firehall Park
Roosevelt Medical Center
Roosevelt Memorial Health Center
Trinity Hospital
CHI St. Alexius Health - Williston Medical Center
Fort Union Trading Post
Missouri-Yellowstone Confluence Interpretive Center
Youngs Island
Medicine Lake National Wildlife Refuge
Big Island
Fort Buford State Historic Site
Brush Lake State Park

Other Places to Stay in Roosevelt County, MT


Roosevelt Medical Center 155 Properties
Roosevelt Memorial Health Center 155 Properties
Culbertson 153 Properties
Brockton 140 Properties
Froid 140 Properties
Bainville 126 Properties
Poplar 67 Properties
Wolf Point 30 Properties
Nellie’s Park 30 Properties
Trinity Hospital 30 Properties
Montana Cowboy Hall of Fame 30 Properties
Firehall Park 30 Properties

Frequently Asked Questions About Roosevelt County?

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

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

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

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 54 properties listed in Roosevelt County 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 54 Roosevelt County, MT Vacation Rentals

Recently Booked Vacation Rentals in Roosevelt County