Apartment holiday rentals in Queen Anne's County

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

My boyfriend and I stayed here this past weekend for a wedding at the Chesapeake Bay Beach Club. The airbnb was a 2 minute drive from the venue. Karin was extremely responsive and such a wonderful host. She ensured our stay was enjoyable and provided local recommendations for us. I never had a problem getting in touch with her and their space was spotless. They provided linens, a coffee maker, snacks, and more! We will definitely stay here again if the opportunity presents itself. Would give more than 5 stars if I could!

My partner and I had a lovely weekend in Chestertown at Beth & Bob’s cottage apartment! They really went the extra mile to make sure we felt welcome and had everything we needed. There were so many thoughtful touches to make sure we were as comfortable as possible. We also loved walking through their beautiful garden. I’m certain we’ll be back again, and we highly recommend this cozy and relaxing spot!

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.

It is the right distance from town to be able to get there easily but also have peace and quiet during the evening/night.

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.

What a lovely place to stay, in a lovely town, taken care of by a lovely landlord. Appreciate everything-will return!

Our second stay at Matthew’s place was fabulous! So close to everything downtown, easy access, great to be able to bring the dog, so clean and quaint. Can’t wait to go back for another Rock Hall stay!

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

My family and I had the perfect weekend. The cafe was fabulous and the sweet store next door was delicious and super friendly. We loved the market across the street and the gift store the apartment had everything we needed and it was very comfortable and clean. would definitely book it again.

Stephen's carriage house was a perfect fit for our weekend getaway in Chestertown. It is a lovely, roomy space for a couple. The living room was easy to relax in, and the bed was quite comfortable. The skylights offer nice natural lighting during the day, and the bedroom was naturally dark - good for restful sleep. All of the provided amenities made the stay convenient, including the wifi, tv, kitchenware and appliances, and shower. We chose this space due to its walkability and its proximity to our favorite restaurant, Modern Stone Age Kitchen, just a couple blocks away. FYI - this space is in the courtyard of a restaurant, so outdoor diners may be heard during the day and evening, but by the time we went to bed the restaurant was closing so it did not affect our sleep. Also, be aware that parking on N Queen St is Residential Only, so be sure to check for signs and park accordingly on nearby streets.

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

Katie was an amazing host and communicator! We loved the space and it was exactly as it was shown. The location was unbeatable. Would love to stay here again!

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

Jordan was a delightful host. A lovely place in a quiet neighborhood. Close to the welcome party and wedding we attended.