195+ Perfect Pickle Stays with Nearby Pickleball Facilities |
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Glenwood pickleball Stays, Resort Rentals, & Homes

About Glenwood Vacation Rentals

Discover over 195 amazing vacation rental options in Glenwood 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 Glenwood.

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 1272.54 ft², with prices averaging US $265 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 Glenwood.

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Top Pickleball-Ready Accommodation Types in Glenwood

Type Count
Vacation Homes 106
Holiday Apartments 43
Cottages 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Glenwood

★ 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 Glenwood with PickleTrip™.

Weather in Glenwood, MD

View the weather forecast for Glenwood before booking your Glenwood 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 Glenwood, MD

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


University of Maryland-College Park
Arundel Mills Mall
Maryland Live Casino
Merriweather Post Pavilion
Walter Reed National Military Medical Center
Rockville Town Center
RIO Washingtonian Center
National Institute of Health Campus
The Mall in Columbia
Xfinity Center
Laurel Park
Mayor of Silver Spring
Sinai Hospital
Holy Cross Hospital
Stevenson University
AFI Silver Theatre
Pimlico Race Course
Linganore Winecellars
Westfield Montgomery Mall
Strathmore

Frequently Asked Questions About Glenwood?

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

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

Discover 5 accommodations with private or nearby pickleball courts in Glenwood. Some of the best destinations to stay and play pickleball are:

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

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

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 195 properties listed in Glenwood 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.


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There are 195 Glenwood, MD Vacation Rentals

Recently Booked Vacation Rentals in Glenwood