Search Chestertown Cottage Rentals from CA $578

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chestertown cottages

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 CA $308
CA $578 total
includes taxes & fees
Feb 27 - Feb 28
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 CA $493
CA $910 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)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is CA $435
CA $787 total
includes taxes & fees
Mar 10 - Mar 11
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

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

10/10 Excellent
"I like the affordability and cleanliness 👍"
Maleek 1-night trip
Posted 1 day ago
Americas Best Value Inn Edgewood

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
16
Accommodation
62 Cottages
Lowest Price
CA $578
Highest Price
CA $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.
How can I find cheap cottages in Chestertown?
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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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