
Vacation rentals with outdoor seating in Dorchester County
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Top-rated outdoor seating rentals in Dorchester County
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House rentals with outdoor seating

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms
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.

Gorgeous, waterfront home - Perfect for Families.
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.

Casa Maria heart of downtown.
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.

Fishing Creek waterfront cottage
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.

Waterfront home with three bedrooms,3 full baths
Really great place with all the amenities of home!

Spacious Gorgeous Waterfront Home with Sunset View
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.

Madison Bay Getaway
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!

House of the Setting Sun/Deal Island Bayfront Home
Once again, our family had an awesome stay in this beautiful home. Definitely will be back..
Apartment rentals with outdoor seating

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND
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!

Welcome to Gilly’s Getaway!
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.

Cozy apartment in Dorchester County
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

Private apt above garage w/ pier and water access
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!

Historic St. Mary's City, MD
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.

Little Slice of Cambridge. 2 bedroom, pet friendly
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.

Farm View Room at Happy Campers
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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- Sandy Point State Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Heritage Shores
- Plantation Lakes Golf and Country Club
- Gerry Boyle Park
- Ragged Point Beach
- Six Flags America
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Sandyland Beach
- Bayfront Beach
- Brownies Beach
- Rose Haven Memorial Park
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Lake Presidential Golf Club
- Guard Shore
- Langford Sand
- Piney Point Beach
- Lane Beach