Holiday rentals with outdoor seating in Queen Anne's County

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

The property, location, house set-up, and communications from the management during our 6 day stay was amazing. Literally the best low-key, relaxing experience I have ever had in recent memory. The house has everything you need for a great peaceful stay, especially if you are just hanging with a small group of close friends. Cooking is particularly awesome, as this property has a great wide open kitchen. The grounds are beautiful. We spent most of our time on the main floor in the kitchen and then on the long beautiful dock where we did some fishing and first time crabbing just for fun. The town nearby and neighborhood is so nice. Not far from Annapolis, MD at all if you want to visit. But honestly, the property alone is so nice to just to stay in and just relax. Great space with some homey accommodations. Big shout outs to one of the property management team members, Melissa. She was so very helpful. Will be back again next year!

Teddi's home was the perfect place to stay while visiting family near Washington College. The home was lovely, beautifully renovated and spotless. We immediately felt at home and appreciated that Teddi had thought of everything that was needed to make our stay comfortable. It was beautifully decorated and we really enjoyed all the unique and fun artwork. The front porch was the perfect place for morning coffee and wine and conversation in the evening. The beds were the most comfortable of any AirBnB that I have ever stayed in!! We will definitely return when we are in the area again!

Karin was very responsive to our last minute booking. The house was as described and directions were clear. We cannot thank the hosts for assisting us during a difficult time.

I definitely recommend this house. More than satisfactory for 6 of us for the weekend. Plenty of room and easy to find.

A group of us went to Chestertown, MD for Memorial Day weekend. The house was exactly as described and the host was friendly. There was a full kitchen with everything you’d need and plenty of linen and towels for everyone. I think the space was perfect and had so much to offer for a great price.

This is a truly exceptional, special place. Something about the details, glam styling, peaceful location, and amazing nearby beaches, nature and restaurants... absolutely one of our favorites of all time. Highly recommended - don't hesitate to book! Even the beds are super comfy and sturdy - the AC and heat work well, the home is perfectly stocked like a family's - not like hotel or your normal minimal/barely functional short term stay. And the bay!! The birds and nature! Can't say enough good things :)

We gace veen staying at Kevin's place for several years bow for our fundraising ride for Moveable Feast. He always goes out of the way to make us feel welcome. The place is perfect for us we are grateful for Kevin, his hospitality, his communication, and his place

This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.

This spot is a very utilitarian unit but perfect for my dog and me. Very easy to walk to town, the bed was very comfortable and it was great having access to the backyard.

Cute and cozy! I felt right at home. Jordan and Danny are very nice folks, the apartment is very well appointed. There is a dock on the property that I should have spent more time on. The bed was a dream to sleep in and I literally overslept my alarm the first day. You will definitely need a car to get around but the apartment is a 3min drive to Safeway, Walgreens, Starbucks, etc. The neighborhood has a homey feel and the apartment has a homey feel which was my jam. My dog had a little accident but I got some carpet cleaner and let Jordan know and she was very understanding. I would definitely stay here again if I am visiting Kent Island.

Deborah was an amazing host, super responsive and incredibly kind. The room was spacious, and we absolutely loved it. Everything was perfect!

We have nothing but praise and gratitude for this lovely river hideaway in the woods after our weeklong restorative "working vacation" there. The apartment is cozy and comfortable, the surrounding area is beautiful, the hosts are lovely, and despite the feeling of privacy and "middle of nowhere" there are great stores, restaurants, area attractions, etc. all nearby. We loved drinking our morning coffee on the floating pier while watching the early morning mist (and chevrons of geese) rising from the river. We loved kayaking and swimming throughout the day from steps away from our apartment door. We loved being greeted by BIRDS BIRDS BIRDS in the nearby trees and feeders every time we stepped outside. And we absolutely loved sitting by the beautiful outdoor chiminea fire at night! We will be back. Thank you Helen, Peter, Sophie, and Moose!

The place was exactly how it was described and pictured. Lived the peaceful atmosphere and the animals. They are soo adorable. You can sit on the screened in porch, drink a cup of coffee and just relax and enjoy the surroundings. Thanks for everything!! Really enjoyed our time there

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!