Kid-friendly holiday rentals in Dorchester County

Teresa’s A-frame was incredible! With the screen doors in place, we got a really nice breeze with the sounds of the ocean and birds. The beds were very comfortable and the whole place was clean. The beach is was a short walk away with wildlife and beautiful views. We would love to return our next time we’re in Maryland!

We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend

My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

This was a great house for our teammates to stay in for the weekend!

nice quiet place to relax and feel right at home

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.

This home is just as advertised...it is very large, great for several families vacationing together! Our group was small so we didn't even make use of all of the space. The house is right on Tanner Creek which is just beautiful for sitting on the dock and relaxing, paddleboarding and kayaking, birdwatching, etc. It's also about a mile from Lookout Point State Park which is absolutely gorgeous. Restaurants and grocery stores are few and far between in this area, so it's a good idea to bring your own food, and the kitchen is well stocked with pots and pans for cooking. If you are looking for a place to relax in a calm and beautiful setting, this is it!

We had a wonderful stay. My girlfriend feel in love with the place the moment we walked in. The kitchen was well stocked with everything we needed. We enjoyed fixing meals and eating at the cozy dining table. The main bed room was very comfortable with plenty of space for both of us. The bathroom was also well stocked. We spent a lot of time chilling either on the deck or in the living room watching movies. We also enjoyed being able to walk to Starbucks and Aldi. We will definitely stay again if available the next time we are in Cambridge.

Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.

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.

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!