Apartments in Chester for Rent

"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"

"Ingrid was a fabulous host. We already plan to return. Beautiful property inside and out. Thank you beyond words, Ingrid!"

"The host was so friendly and easy to communicate with. The accommodations were very clean and organized. The location was perfect; cute shops only miles away, beach access, beautiful views, and short drive to downtown Annapolis!"

"Our home is over 100 years old so staying here was like being home. Great location to the main st shopping and food."

"We had a great stay! Being so close to St. John's is wonderful. This was our second stay. The hosts are gracious and provide everything that is needed. Perfect for anyone needing avoid stairs. In the heart of historic Annapolis, everything is close!"

"Quaint, clean, and new! Highly recommend for anyone needing a 2-3 getaway with great food and atmosphere!"

"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."

"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."

"10/10 for Excellent location, 10/10 for lovely apartment and 10/10 for responsive hosts and extra effort for nice touches. Situated right next door to the entrance of the Naval Academy and about a minutes walk to Market House and the start of the restaurants and pubs. The apartment was clean and well stocked with modern appliances etc. Much better than a hotel room with plenty of space and everything you need for a stay away from home. The only negative is the noise from the neighbours. A...

"Property was clean and comfortable. Host was very responsive. The location is close to many Eastern Shore attractions. Great place if you have a boat or want to kayak on the waterways surrounding this part of Maryland."

"Nice place, nice owners, great location."

"Studio with plenty of space for one. Nicely decorated, ample supplies. Petite front porch to watch the river from. Pam was friendly and welcoming, and I will certainly happily stay here again!"

"Everything was great! We will be back!"

"Property was beautiful! House was very nice and clean. The manager was amazing! Will definitely stay again!"

"Stayed here during wedding night. Host accommodated requests to make the night check in go smoothly. Property is amazing, the Star was everything we thought and more. Would absolutely stay again!"

"Incredible location, super clean. It had everything we needed. This place is just exuding charm and tranquility . The outdoor garden was an amazing place to sit, relax and people watch. Loved it!!"

"great spot, located near town and includes coffee!"

"Especially nice for summer visits."

"Quaint, quiet, clean, and close to restaurants and our wedding venue we attended. Would return and recommend! Thank you!"

"Great communication with the owner. Location was great and close to the Naval Academy. Parking spot was a plus, especially in the area where parking was tight. The place was clean and comfortable. Everything needed was on site. Would definitely recommend."

"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."

"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."

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