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

Search Chestertown Cottage Accommodations

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestertown cottages

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 AU$625
includes taxes & fees
25 June - 26 June
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$948
includes taxes & fees
30 June - 1 July
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is AU$1,941
includes taxes & fees
28 June - 29 June
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is AU$1,070
includes taxes & fees
26 June - 27 June
Secluded Cozy Cottage in Historic Downtown
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
20
Accommodation
64 Cottages
Lowest Price
AU$625
Highest Price
AU$1,941

Frequently asked questions

What is there to do in Chestertown near my cottage?
The ideal travel accessory is a well-planned itinerary. Historical Society of Kent County Maryland is an excellent place to start your exploration of Chestertown.