97+ Perfect Pickle Stays with Nearby Pickleball Facilities |
  1. USA
  2. Kentucky
  3. Ashland

Ashland pickleball Stays, Resort Rentals, & Homes

About Ashland Vacation Rentals

Discover over 97 amazing vacation rental options in Ashland 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 Ashland.

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 541.83 ft², with prices averaging US $202 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 Ashland.

Show more
Show less

Top Pickleball-Ready Accommodation Types in Ashland

Type Count
Vacation Homes 35
Holiday Apartments 21
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Ashland

★ 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 Ashland with PickleTrip™.

Weather in Ashland, KY

View the weather forecast for Ashland before booking your Ashland 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 Ashland, KY

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


Ashland Town Center
Paramount Arts Center
Greenbo Lake State Resort Park
Kentucky Christian University
Camayo Arcade
Highlands Museum and Discovery Center
Central Park
Diamond Links Golf Club
KYOVA Tri-State Mall
Blue Ribbon Lanes
Armco Park
Pendleton Art Center
Sundowner Golf Course
Sandy Creek Golf Course
King's Daughters Hospital
King's Daughters Family Care
SOMC Greenup Family Practice
Marshall University
Big Sandy Superstore Arena
Cave Run Lake

Other Places to Stay in Ashland, KY


Greenup County 188 Properties
Argillite 149 Properties
Wurtland 105 Properties
Greenbo Lake State Resort Park 103 Properties
Boyd County 50 Properties
Grayson 46 Properties
Westwood 42 Properties
Russell 42 Properties
Greenup 40 Properties
Raceland 36 Properties
Cannonsburg 34 Properties
Catlettsburg 25 Properties

Frequently Asked Questions About Ashland?

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

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

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

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 97 properties listed in Ashland in 2026, 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 97 Ashland, KY Vacation Rentals

Recently Booked Vacation Rentals in Ashland