Great Oak Manor — Chestertown, Maryland

Great Oak Manor is a Black-owned luxury boutique hotel overlooking the Chesapeake Bay near historic Chestertown, Maryland. The 1938 Georgian-style manor has 12 individually decorated rooms and suites, plus a separate Carriage House Suite. Its waterfront grounds include a private beach and a broad lawn where guests can watch the sun set over the bay.

Spend the morning over breakfast at the manor, drive into Chestertown for galleries and local history, then return to the waterfront before sunset. On select weekends, the manor brings in visiting chefs for tastings, cooking demonstrations, and hands-on lessons.

Highlights & Amenities

• 12 individually decorated rooms and suites, plus a separate Carriage House Suite.
• Private Chesapeake Bay beach and an expansive waterfront lawn.
• Breakfast at the manor and cruiser bicycles for exploring the area.
• A Taste of Great Oak Manor, a guest-chef series held on select weekends.
• Wellness programming that has included yoga, meditation, and guided tea rituals.

Why Stay Here

Great Oak Manor is a good fit for an anniversary, a solo reset, or a weekend with friends built around a guest-chef experience. You can spend most of the weekend by the bay and still make time for Chestertown’s brick sidewalks, galleries, and waterfront. For a stop rooted in local Black history, visit Sumner Hall, a former meeting hall for Black Civil War veterans that now serves as a museum and community center.

Ownership & Heritage

Owned and operated by husband and wife team Werten Bellamy Jr. and Kellye Walker. The husband-and-wife team purchased Great Oak Manor in 2022 and completed a full renovation of the guest rooms in spring 2024. The manor was originally built as a private residence in 1938 and became an inn in the late 1990s. Under Bellamy and Walker, the property has developed culinary weekends and wellness retreats around their interest in giving guests time to reconnect, learn, and rest.

What to Experience at Great Oak Manor

• Chesapeake Bay sunsets. Take in the view from the lawn or head down to the private beach for a closer look at the shoreline.
• A Taste of Great Oak Manor. On select weekends, visiting chefs lead culinary experiences that can include tastings, demonstrations, and hands-on cooking.
• Wellness retreats. The manor has hosted programs centered on yoga, meditation, tea rituals, and stress management. Check the dates if you’re planning your stay around a specific program.

Things to Do Near Great Oak Manor

• Visit Sumner Hall in Chestertown. This restored meeting hall of Black Civil War veterans is now a museum and community center that shares Kent County’s African American history.
• Explore historic downtown Chestertown. Walk the brick sidewalks of the Historic District, browse local shops and galleries, and stop for an Eastern Shore meal.
• Sail aboard the Schooner Sultana. Check the public sailing schedule for a trip on the Chester River aboard a replica of an 18th-century schooner.
• Go birding at Eastern Neck National Wildlife Refuge. Head toward Rock Hall for trails, migratory birds, and views across the Chester River and Chesapeake Bay.

Frequently Asked Questions

Is Great Oak Manor Black-owned?
Yes. Great Oak Manor is independently Black-owned by Werten Bellamy Jr. and Kellye Walker, who purchased the property in 2022.

Does Great Oak Manor have a private beach?
Yes. The property has a private beach on the Chesapeake Bay.

Is Great Oak Manor adults-only?
The manor describes itself as an adults-only retreat. Its FAQ lists a minimum age of 21 for regular stays and welcomes children for full-estate reservations. Its separate policies page gives a different rule for accompanied teens, so confirm eligibility before booking if anyone in your party is under 21.