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

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

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

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is 2.894.980 ₫
11.514.651 ₫ total
includes taxes & fees
25 Jun - 26 Jun
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is 20.896.492 ₫
35.762.403 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great stay! Could not beat the location in walking distance to so many restaurants, shops, points of interest. Staff was very attentive when needing anything. Our TV cable box was not resetting correctly, maintenance quickly took care of. The only feedback there were 4 people in the room and only 3 towels available. Not an overly huge deal. We’d stay here again!"
Darcie 2-night trip
Posted 13 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
29 Cottages
Lowest Price
11.514.651 ₫
Highest Price
35.762.403 ₫

Frequently asked questions

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What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.