Vacation rentals with a patio in Dorchester County

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Top-rated patio rentals in Dorchester County

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Guest favorite

Rental unit in Cambridge

4.92 out of 5 average rating, 119 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Guest favorite

Home in Madison

5 out of 5 average rating, 20 reviews

Madison Bay Club House

Bring the whole family to this peaceful place to stay. Located on the water at Madison Bay, just south of Cambridge. The laid back idyllic rural fishing village will make you immediately relax. A bird watchers paradise location with cultural and historical significance close by. A short drive to Blackwater National Wildlife Refuge and the Harriet Tubman birthplace and museum. Bay views from every room. Beautiful sunsets. Your own little beach access to launch your Kayak and your own 190' pier.

Guest favorite

Home in Fishing Creek

5 out of 5 average rating, 39 reviews

Fishing Creek waterfront cottage

Waterfront cottage featuring a wall of floor to ceiling windows overlooking the Chesapeake Bay! Catch your own crabs, fish on our dock, relax on the deck, & watch the BEST sunsets of your life- followed by a night sky with countless stars. Hoopers Island was recently named the Best Little Town in MD. This is a laid back watermen community where the closest stoplight is 28 miles away, with NO activities for young children. (The island doesn't have the typical boardwalk, mini golf, shops etc )

Guest favorite

Home in Lusby

5 out of 5 average rating, 83 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Guest favorite

Home in Lusby

5 out of 5 average rating, 20 reviews

ChesapeakeWaterfront - HotTub_FirePit_Kayak_Arcade

Welcome to The Chesapeake Summer House - a newly renovated 4 bedroom, 3.5 bath Lake House with access to the Chesapeake Bay via kayak or paddle board from your private pier. Enjoy everything Southern Maryland has to offer within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, this will become your new go-to retreat from the hustle. Relax and make memories on the water with your family and friends!

Guest favorite

Rental unit in Cambridge

4.95 out of 5 average rating, 21 reviews

Happy Campers Waterfront Suite

Come and experience a relaxing getaway at our Waterfront Suite! Happy Campers is located near the corner of the Choptank River and the Chesapeake Bay, surrounded by acres of farm land. You will enjoy quiet days, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery. A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park.

Guest favorite

Cabin in Lusby

4.99 out of 5 average rating, 80 reviews

Your own private beach? Horizon views of the bay?

Beachfront modern updated Panamabode log cabin with gorgeous views from the home, the hot tub, fire pit, lawn, kayaks. Sit on the swing and watch your family play in the sand on the beach or in the shallow water. Water usually about 3-4' feet for quite a way out. Eagles, pelicans,hummingbirds zoom by, dolphins,crab&oyster boats... Bring your own bed linen & towels (see below for sizes.) No pets allowed at any time. No additional guests or visitors. Limit 3 cars (parking on driveway only.)

Guest favorite

Home in Lusby

4.95 out of 5 average rating, 73 reviews

Soul Oasis - home on the Chesapeake Bay

You can hear the waves of the Chesapeake Bay from the new trex deck. The beach is a short walk away where you can find fossils and sharks teeth and see plenty of nature. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Guest favorite

Home in Lusby

5 out of 5 average rating, 15 reviews

Osprey Eyrie on the Chesapeake Bay

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

Guest favorite

Home in Lusby

4.96 out of 5 average rating, 134 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

Guest favorite

Home in Dameron

5 out of 5 average rating, 98 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Guest favorite

Home in Cambridge

4.97 out of 5 average rating, 32 reviews

Magical Waterfront Home-Dock, Firepit, family fun!

Heron's Rest is a stunning home w/ magnificent water views, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and Historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. 3 night minimum Memorial Day to labor day