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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is €423
includes taxes & fees
8 Oct - 9 Oct
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is €551
includes taxes & fees
21 Sept - 22 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior

3. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is €420
includes taxes & fees
5 Oct - 6 Oct
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Marina

4. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
The price is €754
includes taxes & fees
20 Sept - 21 Sept
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
The price is €326
includes taxes & fees
19 Oct - 20 Oct
Lakefront Home Firepit BWI Marleycreek River
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
"Everyone was polite and the room was extremely quiet. It was relaxing. My daughter and I enjoyed staying at the Historic Inns of Annapolis."
Isabel 3-night trip
Posted 14 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
115
Accommodation
61 Cottages
Lowest Price
€326
Highest Price
€754

Frequently asked questions

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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.