Vacation rentals with a patio in Dorchester County

5 out of 5 average rating, 5 reviews

A cozy living space features a brown reclining sofa paired with a black accent chair. A wooden coffee table centers the room, and a large art print is mounted on the wall. A full kitchen showcases modern appliances and ample counter space, illuminated by overhead lighting.

Guesthouse in Cambridge

Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory medium firm bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near the start of annual races and waterfront activities.

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, 138 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”.

5 out of 5 average rating, 32 reviews

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

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.

4.98 out of 5 average rating, 47 reviews

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

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.

A light gray sofa is adorned with orange throw pillows and a mustard yellow blanket. A decorative pillow featuring a unity design is centered on the couch. A small potted flower sits on a wooden coffee table, enhancing the space's inviting aesthetic.

4.98 out of 5 average rating, 57 reviews

You'll enjoy the The Great Escape in Cambridge!

Styled with a simple elegance and created with comforts of home. We love to share our vacation home! Our favorite is the 8-person dining room table which accommodates meetings, game night & homestyle dinners. Along with the amenities, it's an ideal choice for business travel, intergenerational family trip, golf getaway or a bridal party getaway. Located within minutes of the Blackwater Refuge and the Underground Railroad National Park. Message us for military & teacher discounts!

4.95 out of 5 average rating, 110 reviews

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

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.

5 out of 5 average rating, 24 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

Relax with the whole family at this peaceful place to stay. Whether getting away for a weekend or visiting near by family there is enough room for all. With a large deck space facing the Wicomico River, you can enjoy outside time with family while each of you has something to do. There is a queen bed, queen pull out couch, and twin to king trundle bed sleeping six! Each stay inlcudes free wifi and parking, kitchen with full amenities, grill, beach, dock use, fishing and more!

A charming single-story house is set amidst lush greenery, featuring a welcoming pathway and colorful yellow shutters. The home is surrounded by flower beds and shrubs, providing a serene environment. A chimney adds a traditional touch to the property's design.

4.97 out of 5 average rating, 39 reviews

School Street Retreat: Cozy, artsy, central home

School Street is the perfect spot to launch adventures around Cambridge and the Eastern Shore. You get a full house with two bedrooms, two full bathrooms and beautiful native gardens. Just blocks from Great Marsh Point for boating, fishing, play and river access. Less than a mile to downtown historic Cambridge and the lighthouse/market. Quick drives to Easton, Vienna, Blackwater and more. Also provides great access to historic sites in the area. Come rest, relax and explore!

5 out of 5 average rating, 16 reviews

Magical Waterfront Home Dock, Firepit, Family Fun!

Heron's Rest is a stunning home w/ arguably the best water views in Cambridge from nearly every room, 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 charming historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. Rare location w sunset and sunrise views!

4.96 out of 5 average rating, 149 reviews

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

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!

5 out of 5 average rating, 115 reviews

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

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.

A serene backyard is showcased with green grass and blooming trees. Five Adirondack chairs are arranged around a small fire pit, offering a view of the calm waterway. The tranquil setting invites relaxation and outdoor gatherings.