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) | 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
Jul 24 - Jul 25
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Jul 21 - Jul 22
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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 6 - Aug 7
Total with taxes and fees
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Marina

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.
$657 nightly
The price is $749
Jul 24 - Jul 25
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
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!
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

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Had to park around back with no rear doors but other than that it was a great place to stay. "
Angela 1-night trip
Posted 17 hours ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
22
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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