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 Sept - 20 Sept
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 Rp1.962.730
Rp7.806.669 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 Rp14.136.376
Rp24.193.094 total
includes taxes & fees
8 Jul - 9 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
"We stay here every time we come into Annapolis. It’s a wonderful Hotel wonderful staff and a great location."
David 2-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
30 Cottages
Lowest Price
Rp7.806.669
Highest Price
Rp24.193.094

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.