Beachfront vacation rentals in Queen Anne's County

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.

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House: almost 1800 sq ft. Incredible Water View home across from Kentmorr Beach Bar & Grill/Marina/Fishing Boats near Matapeake State Park & Beach. Perfect for holidays, birthdays, wedding guests, team builds, family fun, fishing, golfing, etc. 4 Bedrooms, 3 Full Baths, 4th Bedroom is large family room with big Internet TVs/fireplace plus a Kitchen, Living/Dining Area, and a huge yard with your very own private beach volleyball court and spacious deck overlooking the Chesapeake Bay.

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.

Sunset at Rabbit Run

Sunset at Rabbit Run is a private waterfront 2 acre property located on the Chesapeake Bay with a semi private beach area and fabulous sunsets. Located just outside of the quaint town of Rock Hall with shade trees in the summer. Fish, crab, kayak and swim in the Chesapeake Bay (weather permitting) while enjoying fabulous sunsets, read a book on the hammock or watch the boats up and down the Chesapeake as they enter Rock Hall Harbor. Your family and/or friends will never want to leave.

Bay View Beach Cottage, plan your family vacation

Bring the family and even the dog.( extra fee). 3 beds to sleep in and for larger families you can rent the separate efficiency on the property. Well equipped kitchen, 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. Dining and grocery close by. Enjoy the bay views of boats going by, the sound of birds, and great sunsets. Minutes to Rt. 50. Close to downtown Annap

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.

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.