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
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

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 AED 823
AED 1,783 total
includes taxes & fees
12 Aug - 13 Aug
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, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,424 total
includes taxes & fees
17 Aug - 18 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Marina

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 AED 1,653
AED 2,751 total
includes taxes & fees
9 Aug - 10 Aug
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

4. Waterfront Home on Marley Creek!

Waterfront Home on Marley Creek!
3.0 star property
Marley
The price is AED 1,315
AED 1,678 total
includes taxes & fees
12 Aug - 13 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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Staff was friendly, courteous and professional. Checking in, directions, and breakfast staff were all very nice and helpful."
James 1-night trip
Posted 3 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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