Group Getaways & Retreat Stays | Chesapeake Paradise

Wonderful Possibilities… with Thoughtful Boundaries

Designed for meaningful time together-not large events or outside crowds.

Chesapeake Paradise is a private, peaceful waterfront retreat created for connection-whether that's time with family, close friends, or a small group coming together with intention. To preserve the experience for our guests, neighbors, and the property itself, we do not host events, parties, weddings, or large gatherings.

Group stays, retreats, and trainings are welcome when centered around registered overnight guests, with only a small number of pre-approved day guests when needed.

If you're planning something meaningful and want to make sure it's a fit, we're happy to connect and guide you.

The easiest next step is to schedule a quick 20-minute call so we can answer questions, talk through logistics, and make sure Chesapeake Paradise is the right fit for your group.

Schedule a 20-Minute Call

Families, Friends & Couples

Reunite, reconnect, and make memories that span generations. Chesapeake Paradise offers plenty of room to spread out and come together—with shared meals, game nights, water fun, and quiet late-night laughs around the firepit. Multiple kitchens and flexible sleeping arrangements across the main house and guest spaces mean everyone has a place to gather and a place to retreat. Whether you’re celebrating a birthday, or gathering “just because,” this is a space where joy feels easy, and nature invites you to slow down and savor it all.

See Photo Gallery

Retreats & Small Group Experiences

Step out of the boardroom and into a setting designed for deeper connection, fresh perspective, and meaningful time together. Chesapeake Paradise offers a peaceful blend of waterfront calm, thoughtful comfort, and inspiring natural beauty for retreats, leadership gatherings, wellness experiences, and small group getaways.

Gather in the open great room, connect over sunset dinners, brainstorm on the screened porch, or simply slow down enough to hear each other again. With private suites, flexible gathering spaces, and the Chesapeake Bay just outside the door, this is where clarity deepens, creativity flows, and people leave feeling more connected than when they arrived.

See Photo Gallery Shawn's Relationship & Self-Love Coaching & Retreats!

Transformational Retreats with Shawn

Step out of self-sabotage, overthinking, and self-doubt into clarity, connection, and Self-Solidarity.

In addition to hosting private group stays, Chesapeake Paradise is home to Shawn Mahshie's immersive retreats-designed to help you step out of self-doubt, reconnect with yourself, and experience deep, lasting transformation.

These are not typical wellness retreats. They are powerful, guided experiences rooted in The Work of Byron Katie and the Wheel of Self-Forgiveness™, where insight becomes real change.

If you're ready for something more than just time away… this is where that shift begins.