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Cottages in Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
$411 nightly
The price is $474
Oct 12 - Oct 13
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Grandma’s Cottage will wrap around you like a warm hug

$388 nightly
The price is $411
Oct 9 - Oct 10
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
$825 nightly
The price is $910
Nov 1 - Nov 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
$583 nightly
The price is $665
Oct 9 - Oct 10
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
$600 nightly
The price is $684
Nov 3 - Nov 4
Total with taxes and fees
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

Find out more about Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
15
Accommodation
58 Cottages
Lowest Price
$411
Highest Price
$910

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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Explore a world of travel with Expedia