Vacation rentals with a patio in Dorchester County

Find and book unique patio rentals on Airbnb

Top-rated patio rentals in Dorchester County

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Superhost

A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.

Apartment in Cambridge

4.9 out of 5 average rating, 130 reviews

Little Slice of Cambridge. 2 bedroom, pet friendly

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”.

Top guest favorite

A white two-story house is set against a clear blue sky, with large windows reflecting the natural light. Surrounding vegetation includes tall golden grasses, contrasting against the sandy beach. The foreground shows a gentle curve in the shoreline, leading up to the house above.

Home in Madison

5 out of 5 average rating, 27 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.

Top guest favorite

The waterfront cottage is viewed at dusk, featuring a spacious deck with a dining area and seating. Illuminated windows suggest a cozy interior. The private pier extends toward the water, lined with post lights, and natural landscaping complements the setting.

Cottage in Deal Island Historic District

4.94 out of 5 average rating, 16 reviews

Cozy "Waterfront Cottage"

Waterfront cottage located on Tangier Sound. Sleeps 6. One Bedroom with queen size bed and queen size pull out sofa in Living Room; queen size pull out sofa in the Sun Room; 1 Bathroom with walk in shower, Kitchen fully stocked with utensils, pots/pans, dishes/appliances, Living Room, Spacious Sun Room, Large open deck, with private pier. Enjoy fishing and crabbing directly off the pier and enjoy drinks and dinner on the spacious open deck. Public boat ramp is 2 miles away with public beach.

Top guest favorite

Two white Adirondack chairs and a small table are positioned on a wooden deck extending over the water. String lights hang above, illuminating the space with a soft glow. The calm water and distant piers are visible under a clear blue sky.

Apartment in Cambridge

4.97 out of 5 average rating, 34 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 walk or bike down the lane to explore quiet back roads and beautiful country scenery. A short 15 minute drive into the town of Cambridge offers unique shops and restaurants, sightseeing and nearby Blackwater Refuge.

Top guest favorite

A wooden dock extends over still waters, reflecting a colorful sky as the sun sets. Soft hues of blue, purple, and orange blend seamlessly, creating a serene atmosphere. The dock is lined with lights along its edges, illuminating the path to the water's edge.

Home in Quantico

4.97 out of 5 average rating, 37 reviews

Sunset Retreat on the Nanticoke

Looking for a true "escape" on the Eastern Shore? This waterfront property has it all. Located just 15 miles from downtown Salisbury, MD, and everyday conveniences, this property is one of a kind! This beautiful house provides the comfort and relaxation you need between all the activities on the property including some of the best fishing on the entire Nanticoke, hiking the 75 acres of woods and waterfront, kayaking or even just enjoying the incredible sunsets as you sit around the firepit.

Top guest favorite

A spacious outdoor area features a custom-built heated pool surrounded by a stone patio. A light blue umbrella provides shade over a white table with several matching chairs. A pool slide and lounge chairs are visible, enhancing the inviting atmosphere.

Home in Cambridge

5 out of 5 average rating, 33 reviews

RELAX, You're on RIVER & POOL time!

Come stay at this centrally-located home with beautiful views of the Choptank River. Enjoy sun filled days by the custom built heated pool and quiet nights by the gas fire pit. Adults and children will love the pool house/game room where you'll find an open air bar, full bathroom, 70" television, shuffleboard, ping pong and foosball. The house is newly renovated with 3 bedrooms 2 bath (1 in pool house) sunroom, and upstairs kids lounge. We are long term 5 Star Airbnb hosts who live nearby.

Top guest favorite

A front porch is displayed with wooden beams and a spacious deck overlooking a lush landscape. Two black wicker chairs provide seating, facing a serene view of trees and Jutland Creek in the distance.

Guesthouse in Ridge

4.93 out of 5 average rating, 46 reviews

The Path

Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet, waterfront oasis guesthouse is the perfect weekend retreat. There is 1 bedroom and 1 bathroom in the house. There is also a pullout couch. There is a large dock for hanging out / sunbathing. There is not a full kitchen, but there is an outdoor grill. You are surrounded by nature - this is a true escape! If you're looking for the perfect weekend getaway, this is it! *Wifi is spotty! Do not rely on it!*

Guest favorite

A welcoming living area features a cozy seating arrangement with a dark green sofa and two light-colored armchairs. A wooden coffee table sits in the center, adorned with a plant and books. Natural light enters through two windows, accentuating the decorative fireplace and neutral decor.

Cottage in Westover

4.92 out of 5 average rating, 52 reviews

Mary’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Mary’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. You simply won’t want to leave! A 30 minute drive to Chesapeake Bay and about 45 minutes to Chincoteague Island There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Martha's Cottage” (check my profile for listing).

Guest favorite

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

Home in Lusby

4.94 out of 5 average rating, 95 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

A spacious living area features large glass windows that frame a panoramic view of the Chesapeake Bay. Natural light illuminates the room, highlighting the wooden ceiling and modern decor. A seating arrangement overlooks an inviting outdoor patio with garden furniture, creating a seamless connection to the outdoors.

Home in Lusby

4.96 out of 5 average rating, 144 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!

Top guest favorite

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

Home in Dameron

5 out of 5 average rating, 110 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

A bright and inviting room features two pink armchairs with a small table between them, set against a backdrop of light walls and hardwood flooring. An elegant chandelier hangs from the ceiling, while a vintage-style dresser and a decorative fireplace enhance the space's charm.

Home in Cambridge

4.86 out of 5 average rating, 64 reviews

High St. Art Gallery Suite

This boutique suite is adjoined to the future home of High St. Art Gallery. This historic home was built in 1796 and is being lovingly restored by three generations of a family committed to creating beautiful, unique and comfortable spaces that can be a retreat away from home. This suite has all the details and delights that will make your stay enjoyable and we hope you will come again and again.