Vacation rentals with a patio in Dorchester County

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Top-rated patio rentals in Dorchester County

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Apartment in Cambridge

4.91 out of 5 average rating, 124 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

A private dock extends over still waters, accompanied by a wooden bench that overlooks the tranquil scene. Soft hues of orange and pink illuminate the sky as the sun sets on the horizon, reflecting on the calm surface of the water.

Cottage in Scotland

4.89 out of 5 average rating, 18 reviews

Cozy Sunrise Waterfront Cottage & Dock

Experience tranquility at this true nature oasis, waterfront retreat adjacent to Point Lookout State Park! Start your day with coffee on the private dock, while bald eagles, herons, and ospreys soar above. Use our kayaks or paddleboard on the creek to relax onto a private beach or explore the open Chesapeake waters for top-tier rock fishing. Catch blue crabs with pots, stroll to the historic lighthouse, or enjoy swimming at the nearby public beach. Nature, adventure & serenity await you here.

Top guest favorite

A serene view of a white house featuring a sloped roof, with large sliding doors leading to a patio area. Two white chairs are placed beside the custom heated pool, which reflects the details of the house and sky. Potted plants add a touch of greenery.

Home in Cambridge

5 out of 5 average rating, 32 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 covered porch with a vaulted ceiling features comfortable blue seating arrangements and a dining table, all overlooking tranquil waters. Large windows allow for panoramic views of the Cambridge Creek, while a ceiling fan provides a gentle breeze.

Guesthouse in Cambridge

5 out of 5 average rating, 14 reviews

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Bring your kayak, paddleboard, or boat and enjoy all Cambridge has to offer or just sit on the end of the pier to watch the sunrise or sunset.

Guest favorite

A two-story gray house is depicted with large arched windows and a welcoming front porch. The structure sits on stilts above the water, while a wooden dock extends towards it, surrounded by quiet water and greenery. The sky displays soft evening light.

Home in Scotland

5 out of 5 average rating, 29 reviews

Bay Front Beach House

Take it easy at this unique and tranquil getaway. Located at the southernmost tip of a peninsula formed by the confluence of Chesapeake Bay and the Potomac River, this house is surrounded by water and has a private beach with shallow waters for sunbathing or playing with the kids. Whether you are looking for nature outings or sunsets on the deck this house really does provide you with all the R&R you could need. Located within biking distance to Point Look Out State Park- a must visit!

Guest favorite

Cabin in Ridge

4.95 out of 5 average rating, 61 reviews

Pizza Friday

Magnificent 26-acre waterfront property just off the Potomac River. This secluded, quiet waterfront oasis boasts four-bedroom and two-full baths with large picture windows offering panoramic water views from almost every room. The large updated kitchen features stainless appliances, ample cabinetry, granite countertops, and a breakfast nook. There is a large sunny dock, a pizza oven, kayaks and a canoe to enjoy the water. If you're looking for the perfect weekend getaway, this is it!

Guest favorite

A well-maintained garden features a variety of plants including herbs, wildflowers, and fruit trees. Gravel pathways meander through lush greenery, leading to the white exterior of the house. Sunlight filters through the trees, creating patches of light across the garden's vibrant landscape.

Home in Cambridge

4.95 out of 5 average rating, 43 reviews

Hambrooks House - Porched Sanctuary near Choptank

Located a stones throw from the Choptank River. Sleeps 8+ people comfortably in 3 well appointed king/queen BR’s and one vibrant sun room. Chill out on our our relaxing wicker-furnished double porches overlooking historic old Cambridge. The home is flanked by calming lavender and fresh herb gardens, peach trees, strawberries, blackberries as well as wildflowers. Just a 2 minute walk to the park and the banks of the Choptank River, famed for its fishing, oysters and sailing.

Top guest favorite

A spacious deck is shown, featuring comfortable seating and surrounded by lush greenery. The scenery includes views of the water and trees, creating a serene atmosphere. Potted plants line the deck, enhancing the natural environment.

Home in Lusby

5 out of 5 average rating, 15 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

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

A view from a window showcases a peaceful scene of the Choptank River lined with greenery. A large tree provides shade, while parked cars are visible on the quiet street. The soft light of sunset casts a warm hue over the landscape.

Home in Cambridge

5 out of 5 average rating, 14 reviews

"Riverside Retreat"

Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview rental is the perfect home base for exploring all that this fascinating city has to offer. With its rich history, vibrant culture, and stunning natural beauty, Cambridge is an ideal destination for relaxation and exploration. Within walking distance to great restaurants, shopping, marinas and a historic downtown area that will both entertain and delight you!

Guest favorite

Home in Lusby

4.96 out of 5 average rating, 141 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, 105 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 sandy beach is visible along the shoreline, with calm water extending into the distance under a clear blue sky. A hammock is suspended nearby among lush greenery, enhancing the serene natural setting. Stone steps lead down to the beach area from the surrounding landscaping.

Cabin in Lusby

4.99 out of 5 average rating, 83 reviews

Your own private beach? Horizon views of the bay?

Modern beachfront Panabode log cabin with stunning views from the home, hot tub, fire pit, kayaks or larger decks. Sit on the swing and watch your family play in the sand on the beach or in the shallow water (usually about 3-4' feet for quite a way out.) Spot Eagles, pelicans, hummingbirds, 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.