Chestertown Cottages

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown cottages

Idyllic Pasadena Retreat With Garden + Hot Tub!

Green Haven

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Glen Burnie

includes taxes & fees

29 June - 30 June

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

Buu T.

includes taxes & fees

30 June - 1 July

Secluded Cozy Cottage in Historic Downtown

Historic District

Tim G.

includes taxes & fees

20 June - 21 June

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

Edgewood

includes taxes & fees

25 June - 26 June

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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

10/10 Excellent

"Lovely time , charming Inn located in historic district with very welcoming staff. It was a delightful experience."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."

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