Family-friendly holiday rentals in Maryland

We loved this Catskills getaway! Even with March rain, we were so cozy and had so much to do both at the house with the sauna, hot tub, and grill hut but also at nearby hikes and breweries. Can’t recommend enough!

William and Liz's place was so enjoyable for a long weekend. We came to the area with our pups to escape the city, ski, show shoe, and enjoy a winter weekend. The house was as described, the hot tub was fantastic and the dogs loved running around on the deck and back yard. The kitchen was fully stocked with all utensils/kitchen tools needed and we found everything very clean. William and Liz were incredible hosts and let us check in early and check out late as there was an ice and snow storm that froze the driveway and made it hard for use to drive our city car out (note, the neighbors helped with plowing all the snow). Additionally, they sent a detailed list of activities and recommendations in the area. Check in and out were both incredibly easy and we felt safe in the neighborhood. We would recommend bringing fire starters in the winter, as we loved using the wood-burring stove. We had a great trip and would highly recommend to all!

Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

We had a great stay at Badlands! Listing was accurate as described. the hot tub and fireplace were perfect after a day of Skiing. Home is close to Belleayre mountain and very quiet! Would recommend staying!

I had a great time at Tracy’s place. The house was really new (much better than the photos). Location was amazing!

Our adult spring break wouldn't have been nearly as comfortable without Danielle and Ely's beautiful home! Myself and three of my closest girlfriends spent a long weekend in the Catskills, making the Barnhouse our home base. Given the dreary weekend, we spent the majority of the trip in the house, utilizing every square space of the property. The kitchen was well stocked and had a lot of resources to make delicious meals and my homemade ice cream. It's clear a lot of love and energy goes into maintaining the space. Even when we ran into hiccups like a small leak in the ceiling and hot tub malfunction, Danielle was very quick to respond to help us navigate the issues. Would definitely stay again!

The place was amazing and featured everything we were looking for. Tammy and Ed were super hosts and made the stay extremely enjoyable. We would stay here again.

My wife and I had a wonderful stay at this cozy cottage in upstate New York. The space was spacious and well-maintained, with multiple floors that offered plenty of room to relax. Everything was spotless, and we especially loved the hot tub and fire pit —it was the perfect way to unwind after a day of exploring. The cottage truly felt like a home away from home. I highly recommend it for anyone looking for a peaceful getaway!

We’ve stayed at Skip’s listings a few times, and it’s been wonderful each stay. Skip is helpful and quick to answer any questions. Andes is the most beautiful town. Highly recommend!

Absolutely loved staying at Arin & Brian’s. This spot is perfect for people with kids/babies! There’s so much to do in the surrounding area including great coffee shops, places to eat & trails to hike. If you enjoy beer, West Kill Brewery is about ~30 mins out and is close by to the mountains if you ski / snowboard. 10/10 spot :)

Beautiful house in a beautiful part of the Catskills. Very peaceful. Great views.

Simply beautiful, charming and cozy stay. The waterfall was amazing, it was frozen but I think that made it even more beautiful, its a short hike to the fall and in my 2-day stay I went about 5 times. Even cold plunged in the fall! The wood stove is so toasty and they have an abundance of wood to last all winter. The kitches has literally everything you can think of and you can tell a food lover lives here. There's even binders with tons of recipes that seems to be made throughout decades, super cool. Overall great stay and just what we needed. Highly recommend!

Robert and Sandra were so helpful in making sure we were able to get the experience we were hoping for. The cabin is beautiful and we enjoyed looking through the photos of its construction. It was clean, comfortable, and very private.

I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

Lovely place to stay in a beautiful peaceful quiet farm property . 15 minute drive to Cooperstown/Brewery Ommegang. Emily was extremely friendly and helpful upon check-in with amazing local recommendations. We went to Origins Cafe for dinner and it was incredible. The space looks nicer than the photos and provides everything you need for a comfortable stay. I would return in a heartbeat.

We had a wonderful stay at Bear Cottage. The house accommodated our family of four, with each of us in our own private bedroom and sharing two full bathrooms. We especially enjoyed lounging on the front porch, just off main street and an easy walking distance to all the stores in town as well as a nice local hike (Tanbark Loop). We also enjoyed the backyard, which was spacious enough for lawn games and included a nice fireplace.

This Airbnb is completely amazing. It is beautiful. It is spacious. It is great for a group. It comes fully stocked with most of the basic things you need like a fully functional kitchen with things like syrup and jam and all of that in there. The host was completely responsive. If you are planning to go to ski, it is close to the mountain. I completely enjoyed our stay.

We had a fantastic time at the cabin. Andres is a great communicator and was very helpful. The cabin was clean and comfortable, we enjoyed the board games and the snowy garden and we found everything we needed to cook. The location is great, close to skiing and stores, but also quiet and picturesque in the woods. We would love to visit again in the future.

Had a great time at the cozy cabin. It's a cabin but still has some nice amenities. Location is somewhat close to road, you can hear occasional cars go by. Still, back by the pond it feels like being away from it all. I had a blast hiking local trails and enjoying the foliage.

This was a absolute gem of an Airbnb. The location was everything my wife and I imagine for our kids to grow up in one day. The plot of land the home sat on was one from a fairytale. Melody was a great host. We will 100% be back to this location.

We recently stayed at Tom’s house while our son played at Cooperstown All Star Village. Tom greeted us upon arrival, offered us great recommendations, provided a tour of the house and any details we would need for our stay. The house and property is generous and peaceful. We felt right at home. It was a seamless ride to CASV, Cooperstown and Oneonta. Make a point to stop at Weaver’s farm for fresh bread, baked goods, deli, grilling items and any other essentials you may need. We highly recommend Tom’s house and would absolutely rent again when we are in the area.

Rob's home is directly across the street from Cooperstown Dreams Park and was the perfect spot for us to watch our 12 year old play. I could easily run my parents home between games to cool off in the A/C. The pool was a welcome spot for several of the boys on the team and the coaches. Rob was very kind, and welcoming. A perfect stay for any family playing at Dreams Park!

We were staying at this rental because our son was playing at Cooperstown All Star Village for the week. We received quite a few notifications leading up, and even including an earlier check-in time. Everything that we needed was available to us, and we truly felt at home. Would definitely rent from them again if we end up coming up here again for one of our other sons. And the added pens, when we arrived where I hit with my younger boys. Thank you so much!

Our family had a great time at John’s place. It was exactly as described, spacious, well equipped, and clean. We spent our days skiing at Hunter Mountain which is a very short drive away, and enjoyed our evenings by the fireplace. It was really cold outside during our stay and we were grateful for the well heated house! Overall, would definitely recommend.