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Featured Cottages in Chestertown

Wye River Cottage and Horse Barn
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Situated on a river, this cottage is within 3 mi (5 km) of Queenstown Premium Outlets, Queenstown Harbor Golf Links, and Queenstown Harbor Golf Club. Chesapeake ...

5/5Exceptional! (6 reviews)
Just what we needed!

"What a lovely entrance driving by the horse farm which is in front of the property! The accommodations were comfortable. We had everything we needed. The property manager was accessible and very responsive prior to our visit so we did not need anything once we arrived. It was a great location not ..."…"

Reviewed on Nov 22, 2020

Wye River Cottage and Horse Barn
Chesapeake Cottages- 2 Quaint Waterfront Retreats
The price is $375 per night from Nov 30 to Dec 1

Situated in Pasadena, this historic cottage is within 16 mi (25 km) of Arundel Mills Mall, Navy-Marine Corps Memorial Stadium, and Anne Arundel Medical Center. ...

5/5Exceptional! (3 reviews)
Perfect Weekend Getaway

"Just what we were looking for! Great spot on the water with the perfect set up to be outside and getaway with a small group of friends. Lauren is incredible responsive and accommodating which made for an ideal stay."…"

Reviewed on Nov 21, 2020

Chesapeake Cottages- 2 Quaint Waterfront Retreats
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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.

Other property types in Chestertown

Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is $89 per night from Nov 30 to Dec 1
4.4/5Excellent! (417 reviews)

"We liked the location and the value, and the friendly staff and the grab-and-go breakfast. Nothing to dislike."…"

Reviewed on Sep 26, 2020

Holiday Inn Express Hotel & Suites Chestertown
Great Oak Manor

Great Oak Manor

3.5 out of 5
10568 Cliff Rd, Chestertown, MD
The price is $179 per night from Nov 29 to Nov 30
4.7/5Exceptional! (31 reviews)

"Beautiful house and the grounds are amazing, we loved sitting on the beach watching the sunset. The property is waterfront."…"

Reviewed on Sep 29, 2020

Great Oak Manor
Inn at Mitchell House

Inn at Mitchell House

3 out of 5
8796 Maryland Pkwy, Chestertown, MD
The price is $150 per night from Nov 29 to Nov 30
4.9/5Exceptional! (24 reviews)

"Fantastic stay! The place is charming and the hosts were amazing"…"

Reviewed on Oct 12, 2020

Inn at Mitchell House
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.