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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 ￥56,423
￥104,166 total
includes taxes & fees
Oct 26 - Oct 27
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A two-story house with a wooden deck, a garage, and a shed in the backyard.

2. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is ￥49,527
￥58,646 total
includes taxes & fees
Oct 27 - Oct 28
Lakefront Home Firepit BWI Marleycreek River
A marina with multiple boats docked, a building with a distinctive yellow roof, and a clear sky.

3. 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 ￥78,365
￥127,572 total
includes taxes & fees
Nov 8 - Nov 9
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.
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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Best in room dining"
Edgar 4-night trip
Posted 20 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
22
Accommodation
61 Cottages
Lowest Price
￥58,646
Highest Price
￥127,572

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that traveling should be stress-free, so if you're chasing cottages in Chestertown at a competitive rate, Expedia delivers. Save cash and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Chestertown?
The simplest way to track down cheap cottages in Chestertown is with Expedia's filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.
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.