Annapolis cottage rentals

This was our 3rd time staying at the Chessie Cottage and it was another great experience. We love everything with the home and enjoy every minute watching the ships pass by and the amazing sunsets. Can’t wait for our next visit!

We were looking for a house with a private beach that felt private and was close to amenities. This house made our vacation very fun and special. The house had stand up paddle boards and a kayak, a hammock and plenty of things that us outdoor folks love to use right on the water. The private beach was perfect and beautiful, especially for sunrise. The kitchen we well stocked and there was enough room for each one in the family to have their own space. We would definitely return for a future getaway!

Location is super convenient to all shopping and downtown. I love being able to access everything while avoiding route 50 which can get really backed up with traffic. Our last stay was at Christmas time so it was fun to enjoy the dock in summer fishing and paddle boarding.

My husband and I really enjoyed our stay!, as a matter of fact we wished we had stayed longer! we did some hiking in a local park with our dog, went bike riding and explored the Kent Island area. the house was really nice, perfect! we had everything we could need and enjoyed using the sauna on our last day. Mark and Karen were wonderful hosts, they even left us freshly baked muffins that my husband could not stop eating!!!

Fantastic location and a beautiful house with lots of room for family. 3 couples and a 2 1/2 year old. Loved the front porch and easy walking access to everything!

Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again.

The house was even nicer than in photos or descriptions. The house very spacious, the pool and pool area were perfect for our needs. The hosts were very gracious, communicative, and easy to work with. I would definitely recommend this property.

Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis.