Woodland Retreat on Kent Island

Woodland Retreat on Kent Island Welcome to Woodland Retreat on Kent Island! Plan your next retreat with us and experience the tranquility and inspiration of Kent Island’s natural beauty.

A private retreat space designed for leadership teams, nonprofit boards, and religious organizations to connect and strategize in a peaceful setting, powered by the Bay Crossing Consulting team, your go-to retreat facilitators. This private and inspiring retreat space was designed by the Bay Crossing Consulting team to support corporate leadership teams, nonprofit boards, and church groups seeking

a peaceful setting to connect, strategize, and grow. Our 4-bedroom, 3-bath home sits on a serene 5-acre wooded lot, providing the perfect blend of seclusion and convenience—just five miles from the Chesapeake Bay Bridge. With comfortable accommodations, high-speed WiFi, and open spaces for collaboration, the Woodland Retreat on Kent Island offers a unique environment for leadership development, strategic planning, and team-building activities. Whether you're hosting an off-site retreat, a visioning session, or a weekend of focused discussions, our space is designed to support your goals. Learn more: https://baycrossingconsulting.com/woodland/.

06/11/2026

In the early days of summer on Kent Island, the days naturally slow down — coffee on the deck in the morning, shared meals in the kitchen, time outside in the yard, and easy trips to nearby parks, waterfront areas, and local restaurants and wineries.

The rest of the time is yours to enjoy the space, the setting, and each other. Woodland Retreat is designed for groups who want to stay together and make the most of their time away without feeling rushed.

Book your stay here: https://www.vrbo.com/3780005

Guests often tell us that some of their favorite moments happen outside the house.Woodland Retreat’s location makes it e...
06/08/2026

Guests often tell us that some of their favorite moments happen outside the house.

Woodland Retreat’s location makes it easy to visit nearby spots like Kent Island South Trail and Matapeake State Park, where a quick walk or bike ride becomes a natural pause in the day.

Check availability and book today at https://www.vrbo.com/3780005.

One thing guests love about Woodland Retreat on Kent Island is the setting: a private, wooded property that feels restor...
05/26/2026

One thing guests love about Woodland Retreat on Kent Island is the setting: a private, wooded property that feels restorative the moment you arrive. 🌳

As we head into summer, it’s a great time to plan a stay where your group can enjoy both the comfort of the home and the outdoor space that comes with it. The Woodland Retreat is an ideal space for intimate family gatherings, friends’ getaways, and more!

Book your stay here: https://www.vrbo.com/3780005

There’s a reason groups choose a home instead of separate hotel rooms: the trip becomes easier, and the time together fe...
05/13/2026

There’s a reason groups choose a home instead of separate hotel rooms: the trip becomes easier, and the time together feels more natural.

Woodland Retreat on Kent Island offers comfortable spaces for shared meals and conversation—without the rush of meeting up in different places. It’s a great fit for family visits, friends’ weekends, reunions, and special events where you want to be together in one spot.

Check availability and book here: https://www.vrbo.com/3780005

05/01/2026

If you’re planning a summer stay, the best trips often start with one decision: choosing a home base that makes everything easier.

Woodland Retreat on Kent Island is a private, group-friendly home for family weekends, friends’ trips, reunions, and special-event travel. With space to gather, space to unwind, and a peaceful setting on Kent Island, it’s a comfortable place to come back to at the end of the day.

Check availability and book today at https://www.vrbo.com/3780005.

If a spring or summer retreat is on your team’s agenda this year, Woodland Retreat on Kent Island offers a calm place to...
04/28/2026

If a spring or summer retreat is on your team’s agenda this year, Woodland Retreat on Kent Island offers a calm place to gather with intention.

It’s a comfortable setting for leadership teams, nonprofit boards, and faith-based groups who want time away to align, plan, and move forward. And if your team wants support structuring the agenda and discussion, property co-owner Shelly Gross-Wade of Bay Crossing Consulting is an experienced facilitator!

View the space and book your dates: https://www.vrbo.com/3780005

Explore consulting and facilitation services: https://baycrossingconsulting.com/services-2/

Quiet mornings. Fresh air. Space to breathe.The Woodland Retreat on Kent Island is just minutes from the Chesapeake Bay ...
04/14/2026

Quiet mornings. Fresh air. Space to breathe.

The Woodland Retreat on Kent Island is just minutes from the Chesapeake Bay Bridge, which means that “vacation mode” is closer than you think. Once you arrive here, the pace changes: a private wooded setting, room to gather, and a calm home base that works for family weekends, wedding guests, or intimate get-togethers.

If you’re planning a trip for spring or summer, check availability here: https://www.vrbo.com/3780005

Introducing your official wedding guest HQ! 💍If you’re attending a wedding on the Eastern Shore this year, The Woodland ...
04/08/2026

Introducing your official wedding guest HQ! 💍

If you’re attending a wedding on the Eastern Shore this year, The Woodland Retreat on Kent Island is an easy, comfortable home base for family and friends. Instead of splitting up across multiple hotel rooms, your group can stay together, share meals, and have space to relax between events.

With multiple bedrooms, plenty of gathering space, and a peaceful setting near the Chesapeake Bay Bridge, it’s a practical choice that makes time together a pleasure. And, in addition to being a more affordable accommodation choice, your stay is just 10-20 minutes from your wedding venue (or other celebratory destination) on Kent Island!

Book Now: https://www.vrbo.com/3780005

04/03/2026

Woodland Retreat on Kent Island is a private, peaceful home base designed for groups who want to stay together and keep the logistics simple. 🏡

If you’re planning any of the following this spring or summer…
· Wedding guest stays
· Family & friends weekends
· Intimate getaways and reunions
· Small group leadership retreats
…the Woodland Retreat offers the kind of stay that makes your getaway easier!

Set on 5 wooded acres near the Chesapeake Bay Bridge, the home offers space to gather, space to unwind, and an easy drive for everyone coming from surrounding areas like Baltimore, D.C., and Philadelphia.

Check availability and book today at https://www.vrbo.com/3780005!

Why choose a house instead of a hotel for your next group trip?A private home gives your group more space, more comfort,...
03/30/2026

Why choose a house instead of a hotel for your next group trip?

A private home gives your group more space, more comfort, and a simpler experience overall. At Woodland Retreat on Kent Island, you can gather in the kitchen and living areas, share meals together, and still have room to spread out—without coordinating multiple hotel rooms or meeting up in a lobby.

It’s a great fit for wedding guest weekends, extended family stays, and small group getaways.

View availability and book here: https://www.vrbo.com/3780005

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Stevensville, MD

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+13014122060

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