Kid-friendly holiday rentals in Dorchester County

Peaceful and private spot just a stones throw from the water. We enjoyed our stay and will be booking again next year! Cozy and comfortable oasis in the woods.

Rustic and charming, the Rusty Anchor was exactly what we hoped for. The screened porch was a favorite hang out spot. The kitchen sink was absolutely adorable. And the host had tons of family friendly amenities available like a baby bath, beach toys, coloring books, and board games. It looks just like the pictures. Her recommendations for the Washington Inn (now Sugar Water), the local beach, and the produce stand were all fantastic. We didn’t want to leave. If you are looking for a low-key, relaxing get-away, this is the perfect place.

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.

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.

Cambridge is so cute and this house was perfect for our stay! Walkable to lots of little shops and restaurants, very friendly neighbors, and an immensely cute and comfortable home.

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!

Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

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

Always responded to my needs. Had a washer and dryer in unit. Continuing to update property. It was very vkean and livable fir the 3 weeks i stayed there.

Its a comfortable place in a quiet neighborhood. Kinda fun but not cramped architecture given you're just below the roof. Nicely decorated with comfortable chairs and a couch. I would stay here again

We actually ended up staying at another property of Mary’s because of a boiler issue at the original place. Mary got in touch immediately & offered an upgrade for the price of our original stay. She made sure we got everything we needed, sending over supplies & solving an issue with the tv. A super responsive host and we much appreciated that! The place we ended up at was right on the Choptank River with gorgeous views and even ducks to feed!!! (Mary supplied the duck food!) A great, relaxing stay!!

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

Perfect location for visit to st Mary’s As described and very well equipped. Thanks to the hosts for quick responses when we had questions!

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.

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.

Our stay was lovely! The property is quiet and peaceful. The apartment is right above the roosters so we could hear them crow every morning, but it didn't bother us. The parking is a bit of a walk from the apartment, but everything was clearly labeled and easy to find. The kitchen had basic pots and pans, plates and bowls, and utensils. But did not have things like cooking oil, salt/pepper, etc. It didn't hinder our stay, but these are mentioned in the listing, so it was noted. Overall, we enjoyed our stay!

The photos are mirror images of the condo. The kitchen and bath are amply supplied with all the items needed, even to prepare meals if you choose. Accessibility features are a bonus when traveling with an individual with mobility issues. Locally, Portside Seafood was a welcome surprise with a delicious menu. It was the perfect place for my sister and me to have some downtime and recharge. Thank you for sharing your beautiful home.

I had an amazing stay at Jen’s apartment! The space was exactly as described—clean, stylish, and super comfortable. The bed was cozy, the kitchen had everything we needed, and the little touches (like the kid’s Conner and lots of board games ) really made a difference. The location was perfect—close to everything but still peaceful at night. Communication with the host was smooth and fast, and they were incredibly helpful with local tips. I’d absolutely stay here again and highly recommend it to anyone visiting beautiful Cambridge!

We had a great stay at Jen's place! It was very spacious and comfortable, and walkable to downtown Cambridge which had plenty of restaurants and bars to explore. The beds were comfortable and the amenities were as described. Jen was a very responsive host and helped out with all our questions. She also offered lots of local recommendations in Cambridge and the surrounding area. I'd definitely recommend Jen's place if you find yourself in Cambridge, MD :)

The perfect place to stay in downtown Cambridge! You step right out the front door to all the shops and restaurants. Beautiful space with all the amenities you could need. Jennifer has thought of everything! Wonderful and responsive host. We will definitely be back for another stay!

Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!