An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is £362
includes taxes & fees
24 Jul - 25 Jul
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is £489
includes taxes & fees
22 Jul - 23 Jul
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House (4 Bedrooms) | Interior

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore

Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
3.0 star property
Glen Burnie
The price is £1,086
includes taxes & fees
6 Aug - 7 Aug
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
The price is £555
includes taxes & fees
24 Jul - 25 Jul
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Front of property

Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is £360
includes taxes & fees
29 Jul - 30 Jul
Waterfront Home on Marley Creek!
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
"We had a fabulous stay in the Robert Johnson House--loved the location, loved the staff, loved the quiet! There was a slight leak in our room (the carpet in one small section was wet) by the third day, probably from the air conditioner working hard in the 100 degree heat, but that was the only thing shy of outstanding."
Sharon 3-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
22
Accommodation
63 Cottages
Lowest Price
£360
Highest Price
£1,086

Frequently asked questions

Why book your cottage in Chestertown with Expedia?
We think that travelling 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 favourite 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.