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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Chestertown cottages

House (3 Bedrooms) | Front of property

Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
$425 nightly
The price is $484
Jul 27 - Jul 28
Total with taxes and fees
Waterfront Home on Marley Creek!
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
$1,282 nightly
The price is $1,461
Aug 9 - Aug 10
Total with taxes and fees
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
House (3 Bedrooms) | Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Aug 8 - Aug 9
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"This place is awesome great location to all the bars and restaurants, not to mention their bar inside very nice great staff, great free breakfast in the morning rooms very spacious and comfortable will definitely be staying again Love this place can't go wrong staying here"
Steven 2-night trip
Posted 2 hours ago
Hyatt Place Kent Narrows & Marina

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
63 Cottages
Lowest Price
$484
Highest Price
$1,461

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.

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