Vacation rentals with outdoor seating in Dorchester County

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Dorchester County outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Four white Adirondack chairs are arranged on a grassy area, facing the tranquil waterfront. A wooden pier extends into the calm river, surrounded by lush greenery and a single tree providing shade. The clear blue sky complements the serene setting.
Home in Cambridge
4.98 out of 5 average rating, 129 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

HaleyRating, 5 stars3 days ago
This is such a pretty little house! It was a perfect size and layout for two families, including a young child and an infant. The house itself is very nice, and it's well-stocked with items you might need. It has a nice view and access to the river, which was great, and it is close to many of the restaurants and other spots in Cambridge we like to visit. I'd definitely stay here again.
Guest favorite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge
4.97 out of 5 average rating, 116 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars3 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Guest favorite
The exterior of a multi-level home features a stone facade with large rectangular windows, allowing natural light to enter. A garage door is prominently displayed, and a front entryway is equipped with a glass door. Small landscaping is visible along the pathway.
Home in Cambridge
4.91 out of 5 average rating, 22 reviews

Casa Maria heart of downtown.

Aaron JRating, 5 stars2 weeks ago
I had a great stay! The place was clean, comfortable, and had everything I needed. I was in town for the Eagaman 70.3 Triathlon, and it was the perfect spot to relax before and after the race. Super easy check-in and a nice, quiet area. Would definitely stay here again.
Top guest favorite
A spacious living area offers views of the Chesapeake Bay through a wall of floor-to-ceiling windows. A cream-colored tufted sofa and two armchairs surround a low coffee table, set on a blue rug featuring an octopus design. Natural light fills the room.
Home in Fishing Creek
5 out of 5 average rating, 49 reviews

Fishing Creek waterfront cottage

AnneRating, 5 stars1 week ago
This was our second year staying here and the place is perfect for our family. The layout and the ADA features were exactly as how they described them to be. This allowed my mother in law to be able to go out on the pier and enjoy her morning coffee. My daughter and I enjoyed the kayaks one morning. It was very relaxing and peaceful.
Superhost
A spacious living area is featured, showcasing a floral-patterned sofa and a glass coffee table. Decorative elements such as potted plants and an ornate display cabinet with collectibles create a homey environment. Natural light fills the space from large windows, enhancing the warm tones of the decor.
Home in Lusby
4.88 out of 5 average rating, 43 reviews

Waterfront home with three bedrooms,3 full baths

AlyssaRating, 5 stars1 week ago
Really great place with all the amenities of home!
Superhost
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland
4.9 out of 5 average rating, 135 reviews

Spacious Gorgeous Waterfront Home with Sunset View

MarkRating, 5 stars3 days ago
Beautiful, large home and location. Great water views from almost every room in the house! We were meeting locals for this trip so we really to know the area, great little beach at the end of the road. We saw a lot of dolphins and rays.
Guest favorite
The exterior of a newly renovated home is displayed, featuring a symmetrical design with a central door and large windows. Lush green grass surrounds the house, while several trees provide shade. A dog is seen on the lawn, contributing to a relaxed atmosphere.
Home in Madison
5 out of 5 average rating, 12 reviews

Madison Bay Getaway

MaryRating, 5 stars1 week ago
Great place for a pet friendly quiet family getaway. The back porch overlooking the water provided a peaceful and relaxing place to enjoy the views. Our family enjoyed the updated kitchen and the welcoming living spaces provided a wonderful place to hangout and spend time together. We enjoyed sitting out on the back porch/sunroom with our dog and taking in the views of the water. The large table on the porch made a great place for family game night and the perfect spot to enjoy some local steamed crabs we picked up. The host was very responsive and made us feel welcomed and at home. Thanks for a great stay!
Guest favorite
A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.
Home in Deal Island Historic District
4.94 out of 5 average rating, 32 reviews

House of the Setting Sun/Deal Island Bayfront Home

DawnRating, 5 stars3 weeks ago
Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

Apartment rentals with outdoor seating

A spacious blue house features multiple large windows and a welcoming porch. Four chairs are arranged on the front porch, inviting relaxation. A tree provides shade, and a small white picket fence borders the property, enhancing the front yard's greenery.
Apartment in Cambridge
5 out of 5 average rating, 12 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

AmandaRating, 5 stars2 weeks ago
Larry's place was perfect. We were able to book with him last minute for the Eagleman and he was able to accommodate our needs. It was a pleasure to meet Larry and have him give us a tour of the home. He was a great host. Would recommend to anyone!
Guest favorite
A wooden sign carved in the shape of a cloud displays the name "Gilly's Getaway" in bright blue lettering. An arrow painted in green indicates the direction to the entrance. A pot of yellow flowers is placed nearby, adding a welcoming touch to the outdoor space.
Apartment in Lusby
5 out of 5 average rating, 7 reviews

Welcome to Gilly’s Getaway!

MarielleRating, 5 stars6 months ago
I visited for a short mother/daughter trip with my 6-year old. This is the BEST place for kids! My daughter loved waking up and visiting the goats and other farm animals every morning, and there are lots of places nearby to look for fossils and explore. Aimee also left us delicious goodies, including freshly baked bagels and homemade jam! The place itself is also extremely spacious and clean.
Top guest favorite
An open kitchen area features modern appliances and a light-colored cabinetry. Cozy seating is provided by a dark leather couch, complemented by a natural wood accent table. A rug spans the floor, enhancing the spacious layout and inviting atmosphere.
Apartment in East New Market
5 out of 5 average rating, 5 reviews

Cozy apartment in Dorchester County

NoahRating, 5 stars2 weeks ago
Jennifer was a great host and the location was beautiful, the street was very quite and wooded, the place had many amenities beds and sofa were very comfortable. They were very friendly and helpful with local tips, information and things to see. Really appreciated it
Top guest favorite
A serene scene along the Choptank River features a wooden deck leading to a dock, with several boat slips visible in the distance. A sculpture of a heron stands amidst a landscaped area, complemented by a bench nestled under a tree, providing a tranquil waterfront view.
Apartment in Cambridge
4.98 out of 5 average rating, 203 reviews

Private apt above garage w/ pier and water access

KamranRating, 5 stars8 months ago
We had an amazing stay at this Airbnb during the GFNY cycling event in Cambridge, MD. The property was spotless and located just about a mile from the event site, which made getting to and from the race incredibly easy. The quiet neighborhood and proximity to the water provided a peaceful and relaxing atmosphere—perfect for unwinding before and after the event. The two-bedroom unit was fully stocked with everything we needed, and the beds were extremely comfortable. Jason was incredibly accommodating, even allowing us a late check-out to fit our event schedule, which was a huge help. I would highly recommend this place to anyone visiting the area, whether for an event or just to enjoy a quiet getaway. We’ll definitely stay here again!
Top guest favorite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park
4.97 out of 5 average rating, 569 reviews

Historic St. Mary's City, MD

AnnaRating, 5 stars2 weeks ago
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
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

JoanRating, 5 stars2 weeks ago
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.
Guest favorite
A serene waterfront scene is captured at sunset, featuring a calming gradient of pink and orange hues in the sky. The sun setting over the water is reflected on a calm surface, while a weathered pier extends into the bay, framed by lush green grass.
Private room in Cambridge
5 out of 5 average rating, 23 reviews

Farm View Room at Happy Campers

MaddieRating, 5 stars2 days ago
Brad & Roseann's Airbnb was beautiful, well-organized and offered a plethora of activities around their property. The views were breathtakingly beautiful! It's essential to stay outdoors for the sunsets. We stayed for 5 days. They were exceptional hosts, very friendly and a delightful couple to meet! They were extremely prompt in their assistance, regularly checked in on us and provided valuable insights on local activities. We highly recommend Brad & Roseann.

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