An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chestertown cottages

A house with a red door, a small porch, and a view of a river with a bridge in the background.

1. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is AU$499
includes taxes & fees
1 Oct - 2 Oct
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A covered patio with a wicker sofa, a glass coffee table, a wooden table, and a bench.

2. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is AU$682
includes taxes & fees
8 Oct - 9 Oct
Idyllic Pasadena Retreat With Garden + Hot Tub!
A wooden deck with wicker furniture, a round table, and a fire pit.

3. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is AU$944
includes taxes & fees
29 Sept - 30 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A marina with multiple sailboats docked.

4. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 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$1,185
includes taxes & fees
27 Sept - 28 Sept
Secluded Cozy Cottage in Historic Downtown
A two-story house with a wooden deck, a garage, and a shed in the backyard.

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AU$433
includes taxes & fees
28 Sept - 29 Sept
Lakefront Home Firepit BWI Marleycreek River
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

8/10 Good
"Superb location. Very tastefully treated. My only suggestions would be to provide more information regarding parking and a technology update in the rooms would be helpful. Plugs for charging was difficult as extensions and adapters were not reliable. High definition TV should be added as well. For the purposes of this trip, we enjoyed our stay very much."
walter 4-night trip
Posted 5 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
115
Accommodation
61 Cottages
Lowest Price
AU$433
Highest Price
AU$1,185

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.