
Holiday rentals with outdoor seating in Dorchester County
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Top-rated rentals with outdoor seating in Dorchester County
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Popular amenities for outdoor seating rentals in Dorchester County
House rentals with outdoor seating

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms
This was a great house for our teammates to stay in for the weekend!

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
Dale is an incredibly proactive and helpful host. He checked in with us several times to ensure we had everything we need and went out of his way to meet us on our schedule to check in and show us around. This is a great spot to relax and look at the ocean or an easy commute to Solomon's Island and all its amenities. You also get access to the community's private beach, which is beautiful and a real asset!

Spacious Gorgeous Waterfront Home with Sunset View
My family of 10 had a great stay here! There was plenty of space to spread out and the location is perfect and serene. We were able to fish out on the dock and caught a few spot! One of the friendly neighbors even stopped by to offer some raspberries from their bush and extra firewood. We did run into an issue after check in with one of the bathrooms, but Karina was quick to respond and sent someone out to handle it as quickly as possible. Thank you for the wonderful 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..

Hoopers Island Victorian with 360 Water Views
Water views, sea breezes and the songs of seabirds-what more could you ask for? If you are like us and enjoy the peace and serenity of nature, this is your haven. Kristin's home made us so happy! The screened porch and open layout of the living room and dining room provided beautiful breezes and views. The house is a perfect blend of modern updates and old architectural charm. The kitchen is well stocked and there is a new deck and outdoor shower that we all loved, especially my daughters after coming back from a run or bike. Additionally, Kristin was an excellent host. She is very thorough in meeting all of your needs. She provides highlights of the area, tips on food and even recipes in her binder. She responds very quickly as well. While the location is remote, it is ideal for people seeking relaxation. We were there for the Ironman and while the drive was somewhat of a distance, it was worth it! We will return! I wanted to stay and just read a book on the porch! Thanks
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

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
Cannot say enough nice things about this place! Hosts were very welcoming (fresh cookies included!) and their space was incredibly relaxing. While the yard and outdoor amenities were shared with the other guests, there was ample space in the yard between the adirondack chairs, lounge chairs, and hammocks. Hosts also have kayaks, floaties, lawn games, and bicycles for guests to use.
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- Sandy Point State Park
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Plantation Lakes Golf and Country Club
- Heritage Shores
- Gerry Boyle Park
- Ragged Point Beach
- Six Flags America
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Rose Haven Memorial Park
- Bayfront Beach
- Brownies Beach
- Sandyland Beach
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Lane Beach
- North Beach Boardwalk/Beach
- Piney Point Beach
- Lake Presidential Golf Club
- Triton Beach