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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is £354
includes taxes & fees
25 Jun - 26 Jun
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
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 £1,012
includes taxes & fees
9 Jun - 10 Jun
Waterfront 5 Bedroom Near Bwi/annapolis/baltimore
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 £488
includes taxes & fees
8 Jun - 9 Jun
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, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is £553
includes taxes & fees
8 Jun - 9 Jun
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Since this is a budget hotel, my expectations were relatively low, but they were exceeded to my pleasant surprise! We booked one night just for a way to break up a long car trip with two small kids for a fairy festival happening nearby. The room was clean and week maintained, the staff were pleasant and extremely helpful, even when our booking wasn't technically paid for because there was some kind of issue with the credit card used by this third party booking, and we had a good and quiet night's sleep!"
Cathy 1-night trip
Posted 1 hour ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
20
Accommodation
63 Cottages
Lowest Price
£354
Highest Price
£1,012

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?
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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.