Woodland Retreat on Kent Island

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Stevensville, MD
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/.

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 wineries, 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

07/29/2026

This fall, Artoberfest 2026 brings Queen Anne’s County to life with a weekend full of local artists, handcrafted goods, live music, food vendors, and community celebration along the Eastern Shore.

When you plan your stay, Woodland Retreat on Kent Island is the perfect home base. Spend your days exploring the festival, then return to our peaceful retreat to unwind.

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

07/14/2026

If you're avoiding the summer crowds, complex hotel check-ins, and travel challenges, treat yourself this Fall to a more relaxed pace at the Woodland Retreat on Kent Island. All the comforts of home await you.

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

07/01/2026

Labor Day will be here before you know it, it's never too early to start planning your long weekend on the Bay. Make Woodland Retreat your home base for one last summer weekend on Kent Island.

Spend your days exploring the Chesapeake Bay shoreline—relaxing at Kentmorr Beach or Matapeake Beach, or taking a short trip across the Bay Bridge to Sandy Point State Park. Then come back to Woodland Retreat and settle into its peaceful outdoor setting—unwind on the deck, gather around the fire pit as the sun sets, or head inside for a friendly game of pool before dinner and time together in the kitchen.

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

06/21/2026

Today is Father’s Day; give the gift of time together!

A stay at Woodland Retreat on Kent Island is an easy way to turn the weekend into a shared experience — morning coffee on the deck, time outside in the yard, a game of co****le, and a quiet walk nearby when the day slows down.

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

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

Address

Stevensville, MD

Telephone

+13014122060

Website

https://www.vrbo.com/3780005

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