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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

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 ￥24,610
￥77,082 total
includes taxes & fees
Feb 10 - Feb 11
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 ￥34,826
￥64,971 total
includes taxes & fees
Feb 4 - Feb 5
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.
The price is ￥61,912
￥110,104 total
includes taxes & fees
Mar 2 - Mar 3
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.
The price is ￥47,641
￥87,306 total
includes taxes & fees
Feb 4 - Feb 5
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

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. "
Michael 2-night trip
Posted 1 day ago
Home2 Suites by Hilton Baltimore/White Marsh

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
18
Accommodation
62 Cottages
Lowest Price
￥64,971
Highest Price
￥110,104

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
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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.