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Search Chestertown Cottages

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Cottages in Chestertown

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
$411 nightly
The price is $474
Oct 31 - Nov 1
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Exterior
Grandma’s Cottage will wrap around you like a warm hug
Grandma’s Cottage will wrap around you like a warm hug
$395 nightly
The price is $419
Nov 3 - Nov 4
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
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. "
United States
shannan t.
$825 nightly
The price is $910
Nov 2 - Nov 3
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Chesapeake Cottages- 2 Quaint Waterfront Retreats
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Nov 3 - Nov 4
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (15)
"Very Annapolis! "
United States
Shannon G.
$709 nightly
The price is $808
Nov 2 - Nov 3
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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"I liked the breakfast because it had cold stuff. And good hot food. Eggs Sausage waffles and juice. "
Ronnie 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
15
Accommodation
58 Cottages
Lowest Price
$419
Highest Price
$910

Frequently asked questions

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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.
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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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