Kid-friendly holiday rentals in Talbot County

Wonderful stay! We had 10 people - 3 generations - and there was something for everyone. The kids (3 and 1) loved the playroom, swings and their adorable rooms. We went on Kayaks and spent a lot of time on the pier catching some fish and a few crabs as well. The yard is a perfect place to read in an Adirondack chair, watch for birds and cook smores. The kitchen is large and we were able to prepare most meals at the house. The screened-in outdoor porch is really nice - with a large dining table as well as comfy seating. The house has water views from most of the rooms. Would highly recommend!

This is our second time staying at Steven’s house. It is a perfect retreat for us.

Relaxing and private home very comfortable. Will definitely rent this house again.

Great house with lots of areas for everyone to have their own space and to be comfortable. The place is very comfortable and the view of the water from the main living area and upstairs bedrooms is beautiful. Though we didn't use the outside amenities due to frigid weather, there are a number of awesome outside spaces as well! Additionally, the house is nicely stocked with items for families with toddlers. Instructions for the house are very thorough and Andrea is responsive to any questions.

We had the nicest ladies weekend on Kent Island! The house was absolutely gorgeous, pristine, and cozy. It was perfect for a group of 7. We enjoyed dinners in the beautiful dining room and chatting in the living room overlooking the water. The island has plenty to offer even in the winter. Kevin and the other hosts were very communicative, friendly, and recommended local restaurants to us. We would definitely return for future getaways!

We had a wonderful stay and felt at home within minutes after checking in. Our favorite space was the kitchen. It well stocked with the cookware and utensils we needed. Plenty of towels and hot water for a nice long shower. I’m a remote worker and the WiFi and bandwidth was more than sufficient for my workload. I visit the area regularly and would definitely book again if available.

The home and host are outstanding - both exceeded our expectations to make for a special trip. The home is beautiful, and the attention to detail was remarkable - decorations, snacks, toys for kids. Highly recommend.

We had an amazing time at this location! We were there for a wedding and my parents joined us so that they could watch our 4 month old. The airbnb was spacious and extremely comfortable for all of us to stay. We were here for St Michael's Christmas Parade weekend and the airbnb was located so conveniently to the down town area, close to the restaurants and shops. We had a blast and most certainly would come back to stay again.

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

This was a fantastic place to spend a relaxing weekend! The hosts were super friendly and very communicative, and the living space was exactly as described. We’re already making plans to come back!

Larry was a fantastic host. He was flexible with our check-in given that we arrived several hours later than planned due to traffic. He went through the entire apartment with us and offered great recommendations for dinner. Larry was responsive to all requests/questions—a definite return location.

Paul was the most responsive Airbnb host we've had! He did everything in his power to accommodate us (even when we booked last minute!) place is great with two pack a plays provided for our young children! We loved our stay- thanks Paul!

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!!

We had a great time enjoying the morning mist of the orchard and the magical sunset of the lake. Great place for a getaway!

There were a lot of thoughtful touches- the bathroom had everything I could have needed. The kitchen was fully stocked and everything I wanted for my morning coffee was all set. The apartment was comfortable and complete. The neighborhood is nice and quaint- I love the cottages and historic buildings of Oxford. Thank you for giving me extra time on Sunday before my performance.

This little studio apartment is ideally located. Downtown St Michaels is far from "urban," but the apartment is central—right on the main street, and the neighborhood can't be beat. A great local roastery-cofee shop almost next door, and an amazing market with great locally raised meats, baked goods, and a wide wine and liquor selection. The town boasts several really good restaurants, too. We're coming back