Waterfront holiday rentals in Deale

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Top-rated waterfront rentals in Deale

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Guest favourite

Cottage

4.99 out of 5 average rating, 148 reviews

Waterfront Chesapeake Bay Sunrises w/Private Pier!

Gorgeous sunrises from your completely remodeled waterfront cottage! Experience fresh Maryland Crabs or fish caught from your private pier & enjoy the peace, serenity and bay breezes from your furnished deck and green space. Enjoy true nature and explore Selby Bay on the South River with our complimentary canoe! Super clean with water views from kitchen, dining, living room & enclosed porch! Situated in a quiet neighborhood within 45 minutes of DC & 15 minutes from Annapolis & the Naval Academy.

Guest favourite

Home

4.92 out of 5 average rating, 12 reviews

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Guest favourite

Home

4.96 out of 5 average rating, 26 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Home

5 out of 5 average rating, 127 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Guest favourite

Home

4.98 out of 5 average rating, 103 reviews

140ft Dock, Pet-Friendly 8 Acre Waterfront Oasis !

3 Bedroom, 2 Bath Waterfront Paradise. This rustic rambler on Broadwater Creek in Churchton, MD, is a family vacation dream. A compound spanning 8 acres with over 700 feet of Waterfront will allow you to fish, crab, paddleboard, kayak, and enjoy the waterfront dream. Located near the small quaint waterman town of Deale, MD, you may never want to leave this relaxing area with direct access to the Chesapeake Bay. Brand new 140ft pier with views straight out to the bay, crabbing, and fishing!

Guest favourite

Cottage

4.97 out of 5 average rating, 171 reviews

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.

Guest favourite

Home

5 out of 5 average rating, 119 reviews

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

Guest favourite

Flat

4.96 out of 5 average rating, 174 reviews

Fall Getaway

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Guest favourite

Cottage

5 out of 5 average rating, 101 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favourite

Guest house

4.94 out of 5 average rating, 318 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Superhost

Home

4.88 out of 5 average rating, 34 reviews

Oyster House Waterfront Retreat - 90 min to DC

This charming, waterfront property is situated on over an acre of scenic beauty. You'll enjoy stunning views from every direction. The large landscaped yard is perfectly shaded with mature trees for hot summer days. Meander down to your deep water private pier to take a swim or throw in your crab pots and enjoy dinner on your screened in porch. An outdoor shower is the perfect way to cool off after a long day on the water.

Guest favourite

Guest house

4.99 out of 5 average rating, 147 reviews

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.