Beach house holiday rentals in Middle River

Waterfront South River Edgewater Sunrises & Beach!

Gorgeous sunrises from your living room & bedroom! Enjoy true nature and explore Selby Bay on the South River! Super clean and charming with water views from kitchen, dining, living room & front terrace! Situated in a quiet neighborhood within 15 minutes from Annapolis & the Naval Academy & 50 minutes from Washington, DC. Your private bedroom & bathroom are located on the first floor of the home. Located directly across the street from our community beach with swimming net and slide, pier & more

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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 3br! Paddleboard & kayak vibe!

Water-lovers dream waterfront cottage 15 min to Annapolis, Navy Academy & 40 min from DC with perfect paddleboarding waters, sandy little beach for kids, fishing gem, pickleball courts & private ramp for boats out your back door. Vacation or commute! Welcome to our favorite place to pop in & out on weekends or lazy afternoons. Grab your laptop, zoom from the porch or office - and still get on the water between meetings! Need to run home to DC for a swimsuit or favorite stuffy you forgot? Done!

Cozy Cottage

Escape to this beautiful cottage overlooking the Chesapeake Bay. Just steps from the beach, this getaway offers water views right from the comfort of the living room. The interior has been remodeled and stylishly furnished, with two bedrooms and one bathroom. This cottage is perfect for couples, small families, or a peaceful solo retreat. Minutes from Downtown Annapolis, the Naval Academy, and other points of interest. NOTE: currently doing yard work; the backyard does not have grass yet

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.

Waterfront 5 Bedroom Near BWI/Annapolis/Baltimore

Welcome to your private waterfront escape—a 5-bedroom, 2.5-bath oasis nestled on the serene shores of Stoney Creek. Located just 20 minutes from BWI Airport, downtown Annapolis (US Naval Academy), and Baltimore, this stunning home offers the perfect blend of comfort, convenience, and coastal charm. Weather you are preparing for your wedding, planning a family getaway, a friends’ weekend, or a peaceful retreat, you’ll find the space, amenities, and setting here to make it unforgettable.

The Waterfront Retreat- *With Sauna and Hot Tub!*

Welcome To Paradise! Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views and a private beach. Enjoy the private guest house, In ground pool, and spacious deck for some of the most beautiful sunsets you've ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.

Heron Point|Kent Narrows 2 Acre Waterfront Escape

Welcome to The Cove at Heron Point — a peaceful 2 acre, 4 bedroom waterfront retreat with endless water views. Located ideally in Kent Narrows, at the Cross Island Trailhead, and close to wedding venues! Enjoy the outdoors, wildlife watching, and nights by the firepit. Perfect for families, with cozy indoor spaces and outdoor fun. Minutes from Kent Narrows and local dining, yet tucked away in nature. Come relax, explore, and unwind at this hidden gem on Maryland’s Eastern Shore.

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.

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.

Mac's Waterfront Wonder

Your family will be wowed by this NEW waterfront 5 bedroom home with a home office, TWO balconies. Indulge in birdwatching (spot a bald eagle? ), boating and jet skiing! Visit Baltimore, DC, Philly, Golf and more! This new home is ideal for large families, long-term stays, or remote work. Three Queen beds; two twins and a bunk bed (full + twin). Sofa bed/queen and air mattresses for five more guests at an additional cost.