Waterfront vacation 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 favorite

Aerial view of a waterfront home nestled along Carr's Creek, surrounded by lush greenery. The property features well-maintained landscaping, outdoor seating areas, and access to a calm body of water, with a backdrop of a peaceful neighborhood and trees in autumn hues.

Home in Deale

4.97 out of 5 average rating, 29 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.

Top guest favorite

A spacious living area features large windows offering unobstructed views of the water. A comfortable sectional sofa is complemented by decorative cushions. A coffee table is positioned in front, with planters adding greenery. A wall-mounted television is visible, alongside a cozy fireplace.

Home in North Beach

5 out of 5 average rating, 135 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 favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 154 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Guest favorite

A scenic waterfront view features a newly constructed pier extending over calm waters. Overlooking the bay, a grassy area is showcased with a fire pit and several patio chairs arranged around it. An American flag gently waves in the background amid a clear blue sky.

Home in Deale

4.98 out of 5 average rating, 106 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

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 favorite

A wooden fishing pier extends into calm water, bordered by lush green trees. The shoreline features natural stone formations and grassy areas. In the background, a traditional cottage is partially visible, set against a clear blue sky.

Cottage in Pasadena

4.97 out of 5 average rating, 172 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.

Top guest favorite

Apartment in Lexington Park

5 out of 5 average rating, 374 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 127 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Superhost

An aerial view captures a single-story cottage set on a spacious grassy area, bordered by tall trees and adjacent to calm water. A dock is visible in the distance, enhancing the natural setting of the property.

Home in Cambridge

4.9 out of 5 average rating, 107 reviews

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8

HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

Guest favorite

Two turquoise adirondack chairs are positioned on a gray concrete pad facing the water. A fire pit is placed nearby, with sandy shore and lush green grass surrounding the seating area. The peaceful waterfront includes a pier and distant homes under a partly cloudy sky.

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 332 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

An aerial view captures a waterfront property surrounded by lush green trees and a spacious lawn. A private dock extends into the water, providing access to the shoreline. Various outdoor seating areas are visible within the landscaped yard, enhancing the serene environment.

Home in Leonardtown

4.89 out of 5 average rating, 35 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.

Top guest favorite

An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.

Guesthouse in Annapolis

4.99 out of 5 average rating, 161 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.

Guest favorite

A charming waterfront property is visible, set amidst lush greenery and colorful foliage. A spacious screened-in porch offers tranquil views, while wooden steps lead to the entrance. Adjoining chairs provide comfortable seating options, enhancing the inviting outdoor space.

Home in Glen Burnie

4.97 out of 5 average rating, 140 reviews

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.