Beachfront holiday rentals in Havre de Grace

2 Bedroom on the Water Close to Baltimore and DC

Take it easy at our unique getaway! Enjoy the best of both worlds - peaceful living by the water, but only minutes away from best entertainment, attractions and eateries. Our Dundalk faves (Jalapenos Mrkt, Seasoned Mariner, Hard Yacht Cafe, Tiki Lees, & Seahorse Inn). Canton/Fells Point - 2.5 miles John's Hopkins & Univ. of Maryland Medical Center - less than 10miles BWI Airport - less than 10miles Baltimore Harbor - less than 10miles Annapolis Naval Academy - 25miles DCA Airport - 45 miles

Peaceful Waterfront Oasis

This peaceful Chesapeake Bay retreat offers an escape from daily life, with stunning bay views providing a calming backdrop at sunrise and sunset. Relax on the deck with coffee, swim right off the dock, or unwind by the water’s edge. For adventure, take out the available kayaks or paddle board to explore the tranquil bay. Afterward, enjoy a rinse in the outdoor shower and soak in the hot tub under the stars. This serene haven blends relaxation and adventure in a beautiful, picturesque setting.

Best kept secret beach-condo on the Chesapeake Bay

Beach. Pool. Sunrise and Sunset. Condo with fantastic view of calm water Betterton Beach. Beach less than 100 steps from front door, with public boat ramp, pier, & bath house. Historic Chestertown (culinary hub w/cute shops) is 15 minutes away. Thoughtfully equipped condo is a great place for families or couples to relax and unwind. Kitchen outfitted for those who like to cook. Public slips (permit required) & pier where you can fish & crab. Beach gear provided. Playground close by.

Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

Flohom 14 | Chesapeake Bay • Pool & Beach Access

FLOHOM 14 | Soteria is a coastal-designed luxury houseboat for two on the Chesapeake Bay at Patapsco Marina in Pasadena, MD. Queen Helix Luxe bed with Parachute linens, sunlit living area, fully equipped kitchen, and Starlink WiFi with a dedicated workspace. Rooftop fire pit, dining table, sectional, and panoramic bay views. Marina includes seasonal pool, beach access, grills, and fishing charter access. Baltimore and Annapolis are a short drive. The quiet you didn't know you needed. ✨

Red Point Lighthouse

Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

Waterfront Wellness - *With Sauna and Hot Tub!*

Welcome To Paradise! 🌊 Private Beach | 🏊 Heated Pool | 🔥 Sauna | 💦 Hot Tub| 🌅 Sunset Views This Chesapeake Bay retreat features a private beach, heated pool, sauna, hot tub, and guest house in a peaceful waterfront neighborhood. Enjoy coffee on the deck, afternoons swimming or kayaking, and evenings watching sailboats pass as the sun sets over the bay. Just minutes from historic downtown Chestertown, shops, restaurants, and marinas for the perfect Eastern Shore getaway.

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.

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

At 3 minutes walk to the beach, this Bayfront condo perched on a bluff in beautiful Betterton is a gem the whole year through. Two level loft condo with three bedrooms (2 BR downstairs, 1 BR upstairs) as well as an ADDITIONAL sleeping loft with two single beds. Two big decks supply scenery for outdoor meals and gatherings. Come for a stay, your cares melt away. The word “peaceful” does not quite do it justice. See for yourself how calm and relaxing life can be.

Bamboo Sands Beach Getaway

Where luxury meets coastal by the bay. A perfect spot to make memories, enjoy the views from the house or the hot tub.... Welcome to Bamboo Sands Villa & Captain’s Quarters, A peaceful retreat on a sandy area of the Chesapeake Bay where families can RELAX & reconnect. Here, serenity and fun flow as easily as the coastal breeze. Enjoy sandy beaches without the crowds, the sounds of waves on the bay without the oceanfront price tag, a coastal luxury getaway...

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

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.