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Private Guesthouse | 7-acres | Near wedding venues

Welcome to The Warehouse! This private guesthouse nestled on Kent Island's Warehouse Creek is thoughtfully decorated, offering rustic charm and unmatched privacy—just minutes from the Bay Bridge. Whether you're attending a wedding, planning a romantic escape, or enjoying a family getaway, this cozy retreat is a perfect, fully stocked alternative to a hotel stay. Enjoy the spacious yard, water views, serene surroundings, and easy access to Kent Island venues, Annapolis, DC, and the Eastern Shore.

The Birdhouse on Swan Creek, Welcome!

An adorable carriage house with panoramic views overlooking Swan Creek -- centrally located, yet private enough to be surrounded by nature. Bird watchers would have a grand time here, with frequent Bald Eagles sightings pre-summer, ospreys, and many other waterfowls at your window in summer. Centrally located: 3 blocks from town beach, restaurants across the road and Rock Hall downtown within walkable distance, next to two local marina. Your private dock through Blue Heron Marsh to Swan Creek.

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

Magnolia Cottage-BlueHeronLandng

QUEEN bed, two TWIN beds, QUEEN sofa bed Sanctuary nestled right at the water's edge. This charming guest house boasts a loft with a Queen bed and two twin beds, and a queen sleeper sofa on the main level, ensuring a restful night's sleep for everyone. There is a fully equipped kitchen and an open concept living area with plenty of seating. A full bathroom, complete with a stacked washer/dryer, adds convenience to your retreat. Embrace the island tranquility as your cares wash away.

Quaint Waterfront- access, Private Shorehouse-unit

Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts private water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants, shopping, trails, and wedding venues.

Waterfront Guest House on 23 manicured acres

Beautiful private guest house on 23 acre waterfront estate, located on Kent Island. Perfect family getaway with private pool, kayaking, fire pit, and more. The estate is just a few minute drive to The Chesapeake Bay Beach Club/Inn, Libbey’s Coastal Kitchen, amazing waterfront restaurants in The Narrows, and Casica Vineyards & Winery. Trip to Annapolis Naval Academy- 30 min, St. Michaels - 45 min. This 1 BR Queen bed, 1 Queen Sofa-bed, 1 Full Futon, 1 Bath accommodates 4 guests.

Owl Cottage - Cozy, Private & Walkable to Town

A renovated 19th century carriage house, Owl Cottage is the perfect combination of historic ambience and modern convenience, all in the center of Chestertown. It has a 1st floor bedroom with king bed, a light-filled 2nd floor living room and kitchenette, and a third story loft, with a queen size bed. There is also a bathroom with shower on the second floor. Beds furnished with luxury linens. There is a private patio with chairs and access to over 2 acres of private gardens.

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

The Crown - Private entrance Apartment.

Kick back and relax in this calm, stylish space, Experience a stunning, upscale private apartment for two, nestled in the serene surroundings of Wye Branch Manor. Enjoy priceless views of cornfields, wooded landscapes, and breathtaking sunsets. Inside, you’ll find a fully equipped kitchen, cozy large bedroom, and a bathroom with a modern stand-up shower The unit features its own central heating and air conditioning systems for year-round comfort.

Casa Cannon

Newly furnished bedroom with queen size bed, internet and cable tv. Shared bathroom and kitchen. Great for interim professionals visiting town for 2 weeks to 6 months, or longer. Application and deposit required. House rules prevail. 950/mth, 300/wk, 120/ day. Conveniently located on Cannon Street in Chestertown. Walk to everything! Pricing is per bedroom, not per person. Max guests per bedroom is 2.

Circa 1700 Chesapeake Colonial Home

On National Historic Register. 4 bedrooms(1Q,1Full,4 twins),3 bath, study, living room, dining room, modern kitchen, farm setting, 22+acres with animals, waterfront with pier. Activities, fishing, canoeing, kayaking,bike trail. Annapolis 15min.

Carriage House

Take it easy at this unique and tranquil getaway. Walking distance to Main Street and the Chesapeake Bay with its amazing sunsets! Plenty of activities, restaurants, Eastern Neck Wildlife Refuge. a beach, boat rentals, bike riding and more!