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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

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
The price is €414
includes taxes & fees
11 Feb - 12 Feb
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
The price is €355
includes taxes & fees
30 Jan - 31 Jan
Grandma’s Cottage will wrap around you like a warm hug
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.
The price is €531
includes taxes & fees
1 Mar - 2 Mar
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"My people mister Ken and Mister Danny always a pleasure"
Allison 3-night trip
Posted 3 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
18
Accommodation
53 Cottages
Lowest Price
€355
Highest Price
€531

Frequently asked questions

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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.