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

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Our top choices for Chestertown cottages

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
The price is NZ$826
includes taxes & fees
25 Aug - 26 Aug
Idyllic Pasadena Retreat With Garden + Hot Tub!

2. 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 NZ$1,105
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats

3. 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 NZ$1,249
includes taxes & fees
4 Aug - 5 Aug
Secluded Cozy Cottage in Historic Downtown

4. Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is NZ$777
includes taxes & fees
17 Aug - 18 Aug
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

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Chestertown Cottages information

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Frequently asked questions

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.