Search Vacation Homes in Chester

"Everything about this property was first class! We had an amazing stay in this comfortable home! Fully stocked kitchen. Body wash and shampoo in each bathroom. All the details covered. The location is awesome. Quick walk to downtown and the Naval Academy. The host was very accommodating and responsive. Can’t wait to stay again!"

"Nice location down town. House was just as the pictures showed. "

"Property is great for families!!"

"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "

"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."

"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"

"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."

"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"

"This home accommodated our multigenerational family of 12 perfectly. The well stocked kitchen was spacious and allowed for multiple people to do either meal prep, eat or cook simultaneously. There are plenty of restaurant options nearby too. Annapolis is an easy 30 minutes away. One evening we inexplicably lost water pressure, but John was a text away and he showed up the next morning and took care of it. He was attentive and a pleasure to rent from. Thank you, John, for a fabulous week!"

"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "

"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...

"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."