Book Chestertown Bed & Breakfast

"The staff are exceptional, nice and helpful.. it is a beautiful little inn. Very pet friendly. We thoroughly enjoyed ourselves"

"Don't mistake Naomi's for a hotel. As a Bed & Breakfast, expect to be welcomed into someone's home, given a large room with a soft bed to sleep in, and woken up to the smells of a warm meal made just for you. Everything was clean and quiet for my entire stay. Any requests I made were humbly attended to and in many cases beyond my expectations. Plus, if you have time to spare, Naomi has an endless supply of stories to share and an ear to listen. I'd highly recommend this B&B to anyone looking for...

"You’re paying for the location, which is excellent. Debo was extremely helpful. Could have had more thorough instructions on internet, front door. Housekeeping could have been better. Chesapeake 1 room was quiet, but extremely small with the tiniest bathroom possible. I would ask for a larger room if available."

"Lovely property with wonderful owners and staff, including three very welcoming dogs. We had a perfect weekend getaway."

"The Annapolis Inn exceed every expectation! The owners are absolutely fabulous. The property is gorgeous and exceptionally appointed. Alex is a gourmet chef who left us wanting more each breakfast. Joe is a tremendous story teller and you will want to sit for hours listening and conversing. Both are wonderful and kind humans who gave us their undivided attention and complete care. This was my first experience at a bed and breakfast and I am forever spoiled. You won’t find better accommodations...

"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...