Beachfront holiday rentals in Queen Anne's County

Private Beach Front Marina House

Beautiful waterfront property with private beach shared with one other family, ideal for family gatherings, located within walking distance of Kent Point Marina and convenience store. Enjoy a relaxing evening with family and friends sitting on the outdoor patio overlooking the Chesapeake Bay. You will have exclusive views of fresh-caught crabs & fish as they come off the boats during Summer. If you enjoy crabbing, fishing, boating, kayaking, swimming - it can all be done from this property.

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Charming Waterfront Cottage on Historic Property

Enjoy a peaceful get-away in a beautifully renovated, historic cottage. The 115 acre property is on a peninsula with over 2 miles of shoreline. This charming home has water access, trails, a canoe, a hammock, and a lovely grilling patio. The cottage is on the private grounds of Whitehall Mansion, built in 1764 as the home of Governor Sharpe. The farm is used for horse boarding and private weddings. Nearby attractions include Annapolis, the US Naval Academy, Washington D.C., and Baltimore.

Bay View Cottage: Perfect for long or short stays

Peaceful cottage and neighborhood, with relaxing views of the bay, close to Annapolis and shopping. Well equipped kitchen and house for long-term or short-term stays...fenced in yard, screened in porch..beach and kid’s park across the street…quiet and relaxing. Community beach (unguarded) to swim or bring your water kayaks or SUPs. Great place to bike as well. Dining and grocery close by. Enjoy the bay views of boats going by, the sound of birds, and great sunsets. Minutes to Rt. 50.

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

Entire River Front Home - 4 Bedrooms 4.5 Baths

Quiet secluded home on the upper Chester River. All bedrooms on second floor. Master Bedroom with deck and private bath. Bedroom with double bed and private bath. Queen suite with queen bedroom and bedroom with 2 twins with private bath between. For more than 8 guests an inflatable mattress in library near half bath and full bath. Perfect getaway for total relaxation. Water access for kayaking and canoeing. Nine miles from downtown Chestertown.

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House – 1,800 sq ft. Chesapeake Bay views. Across from Kentmorr Beach Bar & Grill, Marina & charters, and minutes to Matapeake Beach. Perfect for holidays, wedding accommodations, small family gatherings, fishing trips, or golf getaways. Features 4 bedrooms/3 baths (4th is a large family room with smart TVs & fireplace), kitchen, open dining/living, spacious deck, huge yard, and your own private beach volleyball court.