Family-friendly vacation rentals in Maryland

Lake Effect was the perfect place for our family vacation. The family enjoyed it, we spent most of our time on the dock enjoying the lake and weather, which was amazing. Since I had to work a couple of hours a day before truly vacationing, the internet was somewhat an issue until I found out that if you are streaming on Samsung, the WiFi will be very in and out... so just don't turn on the TV until you are done with work or Streaming using the WiFi. Not sure also, it could have been Comcast, seeing that they have been having issues with their internet services throughout the state and Pa. We certainly were pleased and Paul and his wife were outstanding... We will be back. The Latchford's - Greg and Helen and Family

Great spot for our family vacation! Games downstairs were very fun and movie screen was great. Rick was easy to communicate with. Would recommend!

This was our second time staying here, and we loved it again! The house is in the perfect location and had everything we needed for a great holiday getaway. We felt very comfortable in this cozy home. Maureen is a very kind and responsive host.

Loved staying at Lazy Bear Lodge. Beautiful home with privacy on big property. Hosts were super responsive and gave great local recommendations. Very accessible to hiking and white water rafting.

Great place, nice atmosphere and big with a lot of rooms. Clean and lovely surroundings. I just wish with how big it is, there’s more bath rooms. Hope to come back when its not cold so pool is not cold. 👍🏼

We loved our stay at the Crick House. The kitchen is well designed, the home was cozy, and found the nearby creek very peaceful. During our stay there was a large storm and much of the area lost power. Matthew ensured we were taken care of with extra lamps and flashlights and was very accommodating for the situation.

From the moment we stepped in, we were impressed by the thoughtfully designed interiors that radiated both warmth and elegance. The property truly exceeded our expectations. The spacious layout provided plenty of room for everyone to relax, while the play options for the kids were an absolute delight—they had such a great time! The well-appointed kitchen, with its clean and modern utilities, made cooking feel like a treat. Every detail was clearly curated with care and attention, creating an environment that felt inviting and luxurious at the same time. It added so much joy to our trip, and we’ll always treasure the memories we made here. We hope to return someday!

Brandon’s place was great. It was perfect for our anniversary getaway. The hot tub was clean. The house was clean. We very much enjoyed our time at this place and in the city.

Comfortable is the word to describe this place. Cute, cozy, clean with great walkability. Megan’s instructions were clear, easy and she was more than very responsive. We meandered through galleries, coffee shops and local restaurants. The Navel Academy tour was outstanding. The weather got in the way of our boat cruise. Plenty to see and do with great recommendations from our Airbnb host. Thank you Megan for a great weekend!

Nestled in the tranquil riverside landscape of southern Maryland, just beside the southern Chesapeake Bay, this home is a hidden gem—truly extraordinary in every sense. If you're seeking a brief escape from the bustling energy of Washington D.C. or Baltimore, this haven offers the perfect retreat. We were two families with four children—two young adults heading to college and two spirited middle schoolers—and every one of us, regardless of age, found joy and peace here. From the breathtaking natural surroundings to the simple pleasure of kayaking through calm waters, each moment felt like a gentle reset for the soul. What truly elevated the experience was our host, Shawn. More than just a “super host,” she embodied hospitality in its finest form. Her attention to detail, her care for comfort, and the thoughtful touches throughout the home surpassed even the details of a Hollywood studio setting !

Greg and Pia’s house was absolutely perfect! We’ve stayed at Airbnb’s all across the 50 states and this was the cleanest and most well stocked home we have ever been in! Everything was absolutely spotless. We had the fireplace up and running everyday - it was perfect for our rainy spring stay. It was so cozy! The home is very private and secluded in the woods with an amazing pine lined trail down to the lake access. Our dog absolutely loved being outside and the trail was perfect for our morning walks. Absolutely cozy and perfect. Will definitely stay again!

Ingrid and Jay were very welcoming - they made us feel like family friends instead of Airbnb guests. The carriage home was charming and decorated nicely. It felt like home for the weekend!

Our most favorite Airbnb! Beautiful, peaceful, and close to charming Chestertown. PJ is such an accommodating and gracious host. Cannot wait to come back soon. 💙

Such a lovely, comfortable home. Everything we needed. Loved the location. The neighborhood was extremely quiet and neighbors were friendly. There's a park with walking trails and lake half a mile walk away. The house was perfect. Relaxing. Comfortable beds and bedding. The record player was an added bonus, as were the puzzles and board games for the rainy days. Communication was excellent. Answered any questions quickly and was very helpful. Would definitely stay here again.

Rafi was a very friendly and helpful host. We had a great time in this quiet neighborhood.

This was our second stay with Bob and Lolly in Tall Timbers, and it did not disappoint! Immersed in books and history, this quaint cottage was the perfect getaway. We are looking forward to our next visit!

Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

Mike’s place was perfect for our stay. Close to the bus stop and within walking distance to everything we needed. It was perfect for our weekend away!

House is in one of the best spots for easy in and out of inlet access to beach, shopping, and restaurants. Gives you an extremely personal, and private way to thoroughly enjoy beach life environment. Doug was absolutely amazing from start to finish. Hospitality beyond expectations, which made the stay that much more enjoyable.

We had a wonderful stay! The house is conveniently located close to everything we needed- shops, restaurants, and attractions, especially the huge playground park just a short drive away. The space was clean, cozy, and very comfortable. I especially appreciated how family-friendly the home was. They had a crib already set up for our 9-month-old, which made things so much easier for us. We felt right at home and would definitely come back again!

I enjoyed staying at this location. The view once you enter the condo is fantastic. Access to the beach and to other ocean city restaurants are great very walkable or very very short drive . The building is undergoing some kind of construction so when you walk into the building it’s clearly being worked on and is a bit dusty but once you get in the condo everything melts away. The condo also comes with some beach chairs and umbrellas.

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

Shawn and Terri’s air bnb went above and beyond my expectations! We decided not to stay on the beach this year but I didn’t realize that we’d still be right on the bay! There’s a peer overlooking the ocean that was just a five minute walk away. Not only that, but the community itself was private, peaceful, and had everything you could ever need to stay busy! There were two pools, ball courts, and playgrounds all walking distance. The residents were kind and welcoming. Assateague beach was a five minute drive away and restaurants only a ten minute drive! The main strip of ocean city was super close. The air bnb itself was clean and beautifully decorated. There were extra blankets, amenities, my son loved the cards and coloring books! All in all this was the perfect place to stay.

My family from Michigan was coming to visit and we found the home, it was the perfect spot because everything was close in range. The beds were nice and comfortable, and it was spacious for us all around, because they traveled with 3 children. She was very responsive and I had no problems with our stay here. Would definitely recommend if you’re looking for a place in ocean city, that’s close to everything.