
Kid-friendly vacation rentals in Dorchester County
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Top-rated kid-friendly rentals in Dorchester County
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Kid-friendly house rentals

Soul Oasis - home on the Chesapeake Bay
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.

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.

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

Peaceful Home Away from Home
We stayed 3 nights and this place was perfect. It was myself, my husband and two small children, plus our small dog. The house was the perfect size. Great water pressure, comfy beds and everything was working perfect. We loved the small touches- like they left a towel and washcloth folded in each bedroom. They also left a snack basket and a cute greeting for us! My children really appreciated the snacks. Would absolutely stay here again.

Cove Point Beach Home 1 &1/2 blocks to Beach
Magical. Spent 4 nights with my family (husband and 2 boys, ages 7 and 4). The cottage was pristine. Clean, lovely beach decor but not so much it felt cluttered or dirty. Spacious rooms, 1.5 baths came in handy and lovely screened back deck to enjoy morning coffee/evening glass of wine. We'll appointed, towels/kitchen/beach supplies/etc. Location is fantastic. Property is nicely sized and well maintenence- my boys loved playing in the yard! The association is very quiet, and my boys could ride their bikes safely. An easy walk to the beach for prime fossil hunting. Can't wait to return!!
Kid-friendly apartment rentals

ALL INCLUDED- Chic Move in Ready
Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.

The Grove Studio
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.

2nd floor studio apartment
John and Becky were wonderful hosts! The place was perfect - probably one of the most comfortable beds we've stayed in from an AirBnb host! Would definitely come back for another stay if I'm back in the area. Thank you for your hospitality!

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!

Studio near St. Mary's City
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!

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.
Kid-friendly condo rentals

A Kozy Waterfront Condo
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.

The Drinking Gourd: Stunning Cambridge Penthouse
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 Station House: Upscale Condo in Cambridge, MD
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!

Beautiful 2-Bedroom Loft in Historic Cambridge
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!

Cozy Oxford Getaway
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!
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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