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Chesapeake Paradise TM

A Tranquil Retreat for Unforgettable Moments

Welcome To Chesapeake Paradise

Explore this Property in the Heart of Scenic Chesapeake Bay,

Close to Annapolis, Washington and Baltimore.

Explore the property
5 Ways to Experience Chesapeake Paradise 

Choose the Accommodation Below that Fits for You!

Our large house, romantic suites, & separate Cottage are well-equipped for romantic picnics and leisurely family meals—or enjoy charming local waterfront dining.

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Unforgettable Experience

One of the Maryland's Most Desirable Locations

A peaceful 2-acre waterfront micro-resort, Chesapeake Paradise combines serenity, sophistication, and natural beauty—just 20 minutes south of Annapolis and within easy reach of D.C. and Baltimore. Nestled between Deale and Churchton, Maryland, this stunning point of land offers a quiet escape that’s still close to everything. Whether you’re craving adventure, relaxation, or just the simplicity of a sunset over the bay, Chesapeake Paradise places you at the heart of it all.

Discover the Services we offered

The Essentials and Other Amenities

  • Swimming/ Fishing Pier
  • Spectacular Bay Views
  • Pet Friendly
  • Kayaks/Canoe/Floaties
  • Wifi, Internet, Netflix, etc
  • Well Appointed Kitchens

At Chesapeake Paradise, we believe peace, connection, and beauty aren’t luxuries—they’re necessities. That’s why we’ve created a one-of-a-kind waterfront haven where nature, comfort, and soul-soothing views come together to help you unwind and reconnect—whether with yourself, your partner, your family, or your purpose.

What started as my personal sanctuary on the Western Shore of the Chesapeake Bay has become a beloved 5-star destination for guests from all walks of life. From quiet solo getaways to joyful family gatherings, transformative retreats, and even weddings, this two-acre micro-resort offers more than a place to stay—it’s a place to come back to yourself.

With decades of experience as a coach, retreat leader, and Airbnb Superhost (including a Travel + Leisure award for one of our suites!), I’ve poured my heart into making Chesapeake Paradise a space that truly serves. And if you're looking to go deeper, I also host waterfront retreats and offer optional coaching for those seeking clarity, healing, and a fresh path forward.

Sunrises, fire pits, laughter, stillness. You’ll find it all here.
With love & gratitude,

Shawn

Founders & Creators