Woodland Retreat on Kent Island

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Stevensville, MD
Woodland Retreat on Kent Island

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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/.

10/26/2026

Not every retreat needs a conference room. Sometimes a change of scenery is all you need to bring your team together, step away from the day-to-day and make space for good conversation.

Woodland Retreat offers a private five-acre setting on Kent Island with four bedrooms, three bathrooms and space for up to 10 guests. Gather around the dining table, take a break on the deck, enjoy the outdoor space or wind down with a little friendly competition at the pool table. With a full kitchen, Wi-Fi and plenty of room to spread out, it’s a comfortable setting for leadership teams, boards and small groups to connect and recharge.

Planning a fall retreat? Send us an email at [email protected] to learn more.

10/13/2026

Sometimes you just need a few days away to get everyone together.

Bring the kids, grandkids, parents, and siblings to Kent Island for a fall getaway filled with time outside, local adventures, and plenty of time to simply be together. Explore the Eastern Shore, share a meal around the table, take a walk, watch the sunset or spend a cozy evening catching up at Woodland Retreat.

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

10/01/2026

Looking for a fall getaway without the long drive? Kent Island has plenty to explore, from scenic trails and golf to beautiful views and plenty of ways to enjoy the season. Spend the day exploring, then come back to Woodland Retreat to slow down and enjoy the peace and quiet.

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

09/25/2026

Heading to the 2026 Bay Bridge Run on Sunday, November 8? Turn race weekend into a getaway at Woodland Retreat on Kent Island. After tackling the Chesapeake Bay Bridge on foot, come back to a peaceful, private retreat just minutes from the finish line and shuttle locations. It’s the perfect home base for runners, supporters and anyone looking to enjoy a relaxing weekend on the Eastern Shore.

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

09/16/2026

Fall Girls Weekend, Anyone? Grab your favorite girls and make a weekend of it on Kent Island.

Spend an afternoon exploring the local w**e scene at Cascia Vineyards, Chesapeake Manor Vineyard or Love Point Vineyards & Winery, then head back to Woodland Retreat to keep the good times going.

Think cozy evenings, good food, plenty of catching up, and a glass of w**e under the stars. No packed itinerary required. Just good company and a beautiful place to slow down for the weekend.

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

09/10/2026

Heading to Annapolis to cheer on the Midshipmen this fall? Make Woodland Retreat on Kent Island your home base for the weekend. Just minutes from the Chesapeake Bay Bridge, Woodland Retreat gives you easy access to Annapolis while offering a peaceful place to relax and recharge after the excitement of game day.

See availability and book your stay now: https://www.vrbo.com/3780005

09/02/2026

It's pumpkin spice latte season and you're invited to stay at the Woodland Retreat while enjoying the great outdoors -- from our deck, patios or nearby trails! Grab a cup of your favorite beverage and head out to a farmers market, crab feast, oyster and bulk roasts, stroll our waterfronts and historic main streets, visit regional festivals, athletic events and enjoy our breweries.

If you just need to exhale from daily stresses, book your mid-week stay and enjoy live music at our waterfront w**eries, homemade pastries and ice cream, or salon and spa treatments at a slower, quieter pace.Book your stay now: https://www.vrbo.com/3780005

08/28/2026

Don't just take our word for it. The best part of hosting guests at Woodland Retreat is hearing about the memories they made, the connections they strengthened, and the time they spent together.

Here's what one recent guest had to say.

Ready to experience it for yourself? Book your stay now: https://www.vrbo.com/3780005

08/18/2026

Fall forecast: 100% chance of golf. Cooler temperatures, beautiful fairways, and fewer summer crowds make fall one of the best times to hit the links on Kent Island.

Gather your crew and make Woodland Retreat your home base for a golf getaway. With space for up to 10 guests, there’s room to relax, recharge, and enjoy time together after a day on the course. Nearby golf options like Blue Heron Golf Course and Queenstown Harbor Golf Links make it easy to plan multiple rounds and turn a golf outing into a full getaway.

Pack your clubs and stay awhile. Check availability and book your stay: https://www.vrbo.com/3780005

08/03/2026

Woodland Retreat was designed to be more than just a place to stay. It's where teams can plan, families can reconnect, friends can make memories, and groups can step away from the everyday.

Whether you're planning a:
🌿 Leadership, women's, or wellness retreat
⛪ Church retreat
👨‍👩‍👧‍👦 Family reunion or multi-generational vacation
💕 Friends' weekend
💍 Bridal party getaway
🎣 Fishing trip

Woodland Retreat offers the perfect home base on Kent Island. With room for up to 10 guests and close to waterfront dining, outdoor adventures, and local attractions, it's the ideal setting to relax, reconnect, and create lasting memories.

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

Address

Stevensville, MD

Telephone

+13014122060

Website

https://www.vrbo.com/3780005

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