Photo by Patricia Knorr

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"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
$431 nightly
The price is $498
Dec 14 - Dec 15
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

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
$395 nightly
The price is $419
Jan 1 - Jan 2, 2026
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

Cottage in Stevensville

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.
$794 nightly
The price is $877
Dec 15 - Dec 16
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

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
Dec 15 - Dec 16
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$448 nightly
The price is $511
Dec 15 - Dec 16
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking."
Amy 3-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
18
Accommodation
62 Cottages
Lowest Price
$419
Highest Price
$877

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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