When it comes to luxury travel in Maryland, it’s not all spa treatments and waterfront cocktails—though you can certainly have those, too. For those who want to stay active while indulging in high-end amenities, Maryland offers several destinations that combine tennis with relaxation, refinement, and resort-style living. Whether you’re planning a weekend away or searching for a staycation experience that balances leisure and play, these tennis-centric escapes provide the perfect blend of performance and pampering.
Inn at Perry Cabin
Location: St. Michaels, MD
Vibe: Waterfront elegance with historic charm
Nestled along the Miles River on Maryland’s Eastern Shore, the Inn at Perry Cabin is a luxury resort renowned for its coastal tranquility, fine dining, and impeccable service. The resort’s three Har-Tru tennis courts are set among gardens and lawns, offering guests a private, serene playing environment. Tennis programming is led by Cliff Drysdale Tennis, ensuring top-tier instruction, private lessons, and seasonal clinics.
Why it stands out:
- Breathtaking waterfront views
- Personalized tennis instruction
- World-class spa and sailing excursions
Chesapeake Bay Beach Club
Location: Stevensville, MD (Kent Island)
Vibe: Boutique resort with Chesapeake views
The Chesapeake Bay Beach Club offers a stylish, contemporary escape just across the Bay Bridge. While it's more known for its weddings and waterfront stays, the club offers private tennis access for resort guests, along with beautifully manicured grounds, upscale dining, and a luxury spa.
Why it stands out:
- Exclusive guest access to courts
- Ideal for couples or small-group retreats
- Spa, firepits, and gourmet food pair perfectly with post-match relaxation
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Tose Family Tennis Center at the U.S. Naval Academy
Location: Annapolis, MD
Vibe: Collegiate prestige meets recreational access
For a truly unique luxury sports experience, consider booking a stay in Annapolis and arranging court time at the Brigade Sports Complex—home of the Tose Family Tennis Center. While primarily a training center for Naval Academy athletes, civilians can reserve time on the six indoor and six outdoor hard courts. Play where champions train, then explore downtown Annapolis for fine dining, waterfront walks, and boutique accommodations.
Why it stands out:
- Access to elite-level facilities
- Proximity to Annapolis Yacht Club, restaurants, and spa hotels
- Combine tennis with boating, culture, and history
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Life Time Athletic – Annapolis
Location: Annapolis, MD
Vibe: Modern athletic club meets resort-style service
For travelers who want it all—tennis, spa, dining, and fitness—Life Time Annapolis delivers. With indoor tennis courts, professional instruction, and luxury locker rooms, it offers a retreat that doesn’t compromise on performance. Pair a private lesson with a massage, steam, and a protein-packed brunch at the in-house café.
Why it stands out:
- Climate-controlled indoor courts
- Upscale amenities and spa access
- Drop-in drills, private lessons, and social events
Final Serve: Match Point Meets Mindful Living
Whether you're seeking a quiet escape, a romantic weekend, or simply want to keep your game sharp while relaxing in comfort, Maryland has a selection of luxury tennis getaways worth bookmarking. Each venue on this list offers something unique—be it world-class coaching, breathtaking views, or upscale accommodations that invite you to stay a little longer.
Looking for a second home near one of these premier tennis destinations? Contact us and we’ll help you find your match.