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Find holiday rentals that suit your style

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Apartments
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Cottages
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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chestertown cottages

A wooden deck with wicker furniture, a round table, and a fire pit.

1. 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$879
includes taxes & fees
9 Nov - 10 Nov
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A house with a red door, a small porch, and a view of a river with a bridge in the background.

2. 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, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A building with a black metal gate, a brick pathway, and greenery.

3. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (24 reviews)
"The cottage was perfectly located in the heart of Annapolis. It has many eclectic decorations throughout out it. We enjoyed our stay."
United States
Bridget C.
The price is AU$1,043
includes taxes & fees
9 Nov - 10 Nov
Secluded Cozy Cottage in Historic Downtown
A two-story house with a wooden deck, a garage, and a shed in the backyard.

4. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is AU$472
includes taxes & fees
10 Nov - 11 Nov
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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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.