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Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for Chestertown cottages

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
Rosedale
9.0 out of 10, Wonderful, (2 reviews)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
$455 nightly
The price is $526
Feb 28 - Mar 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
Betterton
$398 nightly
The price is $422
Feb 17 - Feb 18
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
$579 nightly
The price is $660
Mar 2 - Mar 3
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
$495 nightly
The price is $564
Mar 9 - Mar 10
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Good staff and clean rooms "
Deon 1-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
18
Accommodation
62 Cottages
Lowest Price
$422
Highest Price
$660

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.
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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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