Nestled on the outskirts of Chestertown in Maryland, Great Oak Manor is a magnificent 18th-century country-style estate that overlooks the Chesapeake Bay. Offering a relaxing getaway for travelers, the elegant manor house features beautifully appointed guest rooms with private bathrooms, inviting common rooms for relaxing, mouthwatering breakfasts every morning, and warm and welcoming hospitality. Ideally situated for a relaxing getaway or exploring the quaint streets of historic Chestertown, Great Oak Manor promises an idyllic escape from the city. Great Oak Manor

»Guest Accommodations

Guest Accommodations

Great Oak Manor features 12 well-appointed and individually decorated guest rooms with unique country-style furnishings and lovely views. Each room has a distinct character and ambiance with queen or king size beds with pillowtop mattresses, high-quality linens and comforters and comfy pillows. En-suite bathrooms have skylights that flood them with natural light, shower/bath combinations, beautiful vanities with make mirrors, plush towels and bathrobes and luxe bath products. Spacious sitting areas have comfortable seating and sofas, cozy fireplaces, thick carpeting and beautiful French doors leading out the garden. Amenities in every room includes flat-screen HD televisions with HBO channels, hairdryers, bathrobes and complimentary wireless Internet. Maryland Getaways: Great Oak Manor - Photo: Great Oak Manor

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A complimentary breakfast is served every morning in the elegant dining room that overlooks the Chesapeake Bay and includes seasonal fresh fruit, a variety of cereals, homemade baked goods, and a hot entrée, such as French toast, egg strata or quiche. Guests can enjoy breakfast in the dining room or on the lovely terrace in warmer weather, with stunning views of the Eastern Shore. Maryland Getaways: Great Oak Manor - Photo: Great Oak Manor

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Great Oak Manor offers a range of luxury amenities and guest services, including a complimentary breakfast served very morning, hot and cold beverages and snacks available throughout the day, as well as sweet and savory afternoon snacks, and a fully-stocked library from which guests may borrow reading material. Nightcaps and drinks are served in the elegant Music Room in the evenings, there is a waterside fire pit for relaxing under the stars, and guests have access to kayaks, canoes, paddleboards, and cruiser bicycles to enjoy. The marina next to the Manor offers a variety of facilities and services to which guests have access, including a swimming pool, a fitness room, a 9-hole golf course and tennis courts. Maryland Getaways: Great Oak Manor - Photo: Great Oak Manor

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»Weddings & Events

Weddings & Events

Great Oak Manor provides a beautiful waterfront setting for destination weddings, as well as a range of wedding packages to suit every taste and budget. From quiet elopement ceremonies for two to larger event outdoors surrounded by family and friends, Great Oak Manor can custom design a wedding package to suit every need and they are available throughout the year.

Great Oak Manor also offers exclusive packages for special occasions from birthdays to anniversaries, which include dining at excellent local restaurants and exploring the surrounding area. The Anniversary Package includes sparkling wine, a beautiful floral arrangement, and chocolate-covered strawberries, while the Romantic Package features chilled sparkling wine, chocolate covered strawberries, fresh flowers, and two keepsakes Great Oak Manor bathrobes. The Birthday Package offers a fresh baked small cake or cupcakes for two, and a bottle of white, red, or sparkling wine, and the Blue Crab Chesapeake Charters Package features a pre-made reservation for a chartered sail from the Rock Hall Harbor out into the Bay. Maryland Getaways: Great Oak Manor - Photo: Great Oak Manor

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»Plan this Vacation

Plan this Vacation

The historic town of Chestertown and the surrounding Chesapeake Bay offer a variety of activities and attractions to enjoy from relaxing sojourns to outdoor adventures. The Chesapeake Bay offers sunset cruises, fishing, boating, canoeing, and kayaking, while the historic downtown district of Chestertown is home to the Farmer’s Market on Saturday mornings in Fountain Park in Chestertown, several excellent antique shops, museums, galleries, and boutiques. Attractions in the town and surrounding area include the historic Washington College, the Eastern Neck Wildlife Refuge, the Garfield Center for the Arts at the Prince Theater, the Mainstay, and the Church Hill Theater and Music in the Park, which is held every other Saturday in Chestertown’s Fountain Park during the summer. Driving tours and trails include the National Scenic Byway and the Chesapeake Wine Trail, as well several wineries and estates that produce fines wines and luxe food. Local annual events in the area range from the Chestertown Tea Party Festival and the National Music Festival to the Pirates and Wenches Fantasy Weekend and the Chestertown Harry Potter Festival.

Back to: Romantic Getaways in Maryland Address: 10568 Cliff Road, Chestertown, MD 21620-4115, Phone: 410-778-5943, website Maryland Getaways: Great Oak Manor - Photo: Great Oak Manor

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Maryland Getaways: Great Oak Manor