Photo by Assya A
Search Cottages in Chestertown
Check availability on Cottages in Chestertown
Compare 39 Cottages in Chestertown with updated reviews, rates, and availability.
Amazing views, short walks to great dining!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (76)
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
10.0 out of 10, Exceptional, (81)
The Heron's Nest at Atlantic Marina
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (286)
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (22)
Waterfront River Cottage for 2, dog-friendly
Waterfront River Cottage for 2, dog-friendly
9.2 out of 10, Wonderful, (7)
Secluded Cozy Cottage in Historic Downtown
Secluded Cozy Cottage in Historic Downtown
10.0 out of 10, Exceptional, (6)
The price is AED 1,377
AED 2,370 total
includes taxes & fees
7 Jan - 8 January 2025
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (97)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types 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, (205)
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, (23)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels
5/5 Excellent
"Historic and gorgeous "
A verified traveler stayed at Historic Inns of Annapolis
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Cottages in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Apartments in Chestertown
- Guest Houses in Chestertown
- Motels in Chestertown
- RV Parks in Chestertown
- Houseboats in Chestertown
- B&B in Chestertown
- Condo Rentals in Chestertown
- Villas in Chestertown
- Farmstay in Chestertown
- Cabin Rentals in Chestertown
- Lodges in Chestertown
- Hotels