Apartment holiday rentals in Queen Anne's County

Comfortable beds, spacious layout, great shower and great scenery

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

This is a great large open suite. Very comfortable and attractive with everything you might need and an easy walk to restaurants, theatre, and riverfront. We’ve stayed here several times as well as in the house next door hosted by the same lovely people. Highly recommended.

Convenient location in a quiet neighborhood. Walkable to waterfront, restaurants, and shops. Well-stocked kitchen. Bathroom is quite small. Kelly is a thoughtful and generous host, and knows how to make his guests feel welcomed.

We needed a quiet and private space to relax. Jordan’s space was all of this. We stayed here for a month and hardly ever heard Jordan and her family. Jordan was quick to respond if we had any questions. The bed was very comfortable and the views of the water were nice.

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!

We loved the apartment. It was located in downtown Chestertown. Lots of fun stores and great restaurants. Julie was a wonderful hostess. We would definitely stay here again.

The online photos honestly don’t convey how wonderful this place is. Pristine kitchen and bath, private back patio, fluffy new towels, robes in the closet and the kitchen has everything. The location could not be more convenient for walking in town and Katie’s book of restaurants and things to do was spot on. We will definitely be back.

We had a very positive experience. The apartment’s rooms were clean and comfortable, and it always seemed sunny and nice. Most furnishings felt relatively new and fresh, and they even had a baby gate for our toddler. The downtown area is very walkable from the apartment, and there is a nice cafe right across the street. We didn’t require much contact with the hosts, but they promptly responded to the few messages we sent. We’d definitely stay here again when we visit in the future.

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

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.

Checkin/Checkout were super easy. Our suite was very cozy and clean. It had all the essentials and was conveniently located in the middle of town. Flash (our dog), my wife, and I really enjoyed our stay! We definitely recommend Deborah and Cinammon By the Bay.

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!

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!

First of all they were excellent host. We are very big on hospitality and if we had to grade them on a 1-10 scale I would rate them a 20. Beautiful home made me and my family felt welcomed. If we needed anything or had any questions they instantly responded. Most of all the nice big beautiful hot tub is what I would have to say we enjoyed the most. Being that we’re only a little under a hour away we will be back.