Search B&B in Chester

"The owners were great hosts"

"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."

"We loved that the historic house was built by the son of freedenslaved African Americans."

"The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The...

"It was the perfect spot when attending a wedding in Annapolis. The host was extremely accommodating and the house with views of the river were perfect for friends & family to gather. Definitely would love to return."

"Wonderful stay at this cozy B&B. Proprietors are kind and helpful, and make an amazing breakfast. Rooms are bright and spacious with all the necessary amenities. Looking forward to visiting again during summer months. "

"I booked the trip to celebrate an anniversary weekend away with my husband. The property came up through a Yelp review so I checked it out. I was impressed with the location, the detail to cleanliness, and the commitment to the environment. Once I booked the room, the innkeepers were very helpful in offering things to do and places to eat, as well as offering to help make our anniversary stay more memorable. Once we arrived, Cory took the time to greet us as we came in and share some of the...

"It was amazing. The place was nicely decorated. Food was great. Highly recommended."

"Wife and I stayed 3 days for 41st anniversary. Bob and Tracy are wonderful hosts. "

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

"Beautiful resort, outdated but clean. We went on the weekend before ownership changed so the menu was limited and the breakfast was undercooked but the server was AWESOME! He remembered us and catered to us like we were the only customers."

"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 sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."

"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!"

"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."