Kid-friendly holiday rentals in Kent Island

we were at ease and comfortable staying at Vicki's place for a wedding nearby. all the accomodations were great. kitchen was wonderful and stocked. very clear checkin and checkout instructions. beds were so comfy, especially the mattress in the master suite. my parents liked it so much, they checked the manufacturer and purchased the exact same one for their own bedroom at home!

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

The house was clean and perfect place to stay while we visited friends in the area. Reg and Julia were very nice and communicative!

Eric’s place is wonderful in a very quaint neighborhood! Communication with Eric was excellent. The home is very comfortable and accommodating for families and large groups visiting. We were in town checking out the DC sites and the proximity from the home to the Glenmont Metro was close and easy. The kitchen is well equipped with just about every appliance or cooking utensil you could need to whip up a meal. There’s two washer and dryers and plenty of towels which is really convenient for large groups. The backyard hot tub was nice for relaxing especially after a 20,000 step day exploring DC (phew!) I would most definitely recommend this home and host!

Incredible, serene home with thoughtful design and furnishings. Our family loved the house, which served as a great space to gather over meals, games and stories. The deck on two sides of the house, with great seating, provided a gentle welcome to the nature around with harbor views in the distance. As seasoned Eastern Shore folks, this was an introduction to Rock Hall, which we really enjoyed, especially the refuge. Thanks, Lauren, for your insightful planning and attentive care for the house and your guests.

We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

Penny is an incredible host who really goes above and beyond! I greatly enjoyed my stay.

Lisa’s place was amazing! My daughter and I had a great visit. The location is perfect for going into Annapolis. We will definitely be back. Thank you for a great few days!

Had an amazing stay here! Bob and Beth were extremely responsive hosts and provided a lot of clear instructions on how to find the carriage house. It was very clean and spacious and had a great coffee set up. The surrounding gardens are so lovely! Was quiet and walkable to the local downtown area

A beautiful, elegant space with plush couches, super comfortable king bed and everything you could possibly need! Even extras like a fireplace and dual headed shower you can actually walk around in. The kitchen area was very well stocked and neatly layed out. Great location near so many things to do in Baltimore. Instructions were clear and things well labeled. We felt so well rested and had so much fun in the area. John was thorough with instructions and great to communicate with. If we have the chance to go back Baltimore we’re definitely staying here! I’ve always wanted to stay in a city apartment with tall ceilings and (some) brick walls and it was just so lovely! 10/10!!!!!!

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Clean and friendly let us know where Good places were to go to spend time. Dan was great and were respectful of our privacy 👍🏼

Kimberly's place is in a great location and is walkable to many pubs and restaurants, as well as to downtown Annapolis.

We had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!

Ellen’s condo was absolutely perfect for Commissioning Week. The location couldn’t have been better—within walking distance to fantastic restaurants, the Naval Academy, and Graduation at the Navy-Marine Corps Memorial Stadium. The coffee shop downstairs was a delightful bonus, and the underground parking was a major perk. Ellen provided clear and detailed instructions about the condo and guest expectations, making everything easy to understand and stress-free. The condo itself is beautifully and tastefully furnished, with all the essentials thoughtfully provided. The in-unit washer and dryer were a huge convenience. The bathroom was spacious and well-appointed, complete with shampoo, conditioner, and body wash. What I appreciated most was how quiet and peaceful the condo was—it offered a true retreat. The private patio was perfect for enjoying a morning coffee or an afternoon cocktail. I would absolutely stay here again.

We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

Exactly as advertised. Quiet and convenient.

We were in town for Maryland Deathfest. The place was located within walking distance of everything we needed.

We had a great time once again staying here. It is just steps from the main gate of USNA and the downtown activities and restaurants. Caite was also responsive and very flexible with us and our needs.

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!

Great apartment! Sean’s apartment is very comfortable and tastefully decorated. It is completely quiet at night and the bed is good. There is a good vibe in the neighbourhood and the apartment is less than five minutes from a Green Line metro station that will take you directly to the best art museums in the city. Sean and his co-hosts are very helpful and responsive. I hope to come back to Washington one day and if that happens, I will definitely try to book Sean’s apartment again. Thank you Sean, Megan and Loren for all your helpfulness and a lovely stay!