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Chestertown Holiday Rentals
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Holiday Rentals in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (202)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
10.0 out of 10, Exceptional, (22)
'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (175)
The price is HK$685
HK$1,591 total
includes taxes & fees
24 Nov - 25 Nov
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
10.0 out of 10, Exceptional, (48)
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (94)
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (40)
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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Other types of properties in Chestertown you may be interested in
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (727)
The price is HK$830
HK$922 total
includes taxes & fees
15 Dec - 16 Dec
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
7.2 out of 10, Good, (320)
The price is HK$581
HK$645 total
includes taxes & fees
1 Dec - 2 Dec
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
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.
Find out more about Chestertown
Find out more about Chestertown
Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:
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Look no further and take a look at our great range of rental properties in Chestertown!
Recent reviews of Chestertown properties
Recent reviews of Chestertown properties
5/5 Excellent
"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."
A verified traveller stayed at Historic Inns of Annapolis
Posted 1 day ago