Where to stay
in Chestertown
Best places to stay for families
Comfort Inn & Suites Chestertown is a hotel featuring free parking and free full breakfast that guests like for its helpful staff and clean rooms. Red Roof Inn & Suites Chestertown is a hotel featuring free parking and laundry facilities that guests like for its helpful staff.
Recommended hotels
Best places to stay with pools
The Lodge at Great Oak Landing is a lodge featuring a seasonal outdoor pool and a golf course. You'll also be close to Chesapeake Bay and Northern Chesapeake Bay.
Recommended hotels
Explore a world of travel with Expedia
- Hotels near Washington College
- Hotels near River Arts Chestertown
- Hotels near Historical Society of Kent County Maryland
- Hotels near Garfield Center for the Arts at the Prince Theater
- Hotels near Wilmer Park
- Hotels near Rolphs Wharf Marina
- Worton Hotels
- Motels in Worton
- Church Hill Hotels
- Motels in Church Hill
- Kennedyville Hotels
- 4 Star Hotels in Kennedyville
- Apartments in Kennedyville
- B&B in Still Pond
- Still Pond Hotels
- Cabin Rentals in Still Pond
- Great Oak Landing Hotels
- B&B in Great Oak Landing
- Motels in Great Oak Landing
- Pet-friendly Hotels in Great Oak Landing
- Crumpton Hotels
- B&B in Crumpton
- 4 Star Hotels in Crumpton
- 3 Star Hotels in Crumpton
- Hotels near Crumpton Auction
- Edesville Hotels
- Tolchester Beach Hotels
- Hotels near Crow Farm and Vineyard
- Price Hotels
- Betterton Hotels
- Cottages in Betterton
- B&B in Betterton
- Vacation Homes in Betterton
- Condo Rentals in Betterton
- 5 Star Hotels in Betterton
- Motels in Betterton
- Rock Hall Hotels
- B&B in Rock Hall
- Houseboats in Rock Hall
- Pet-friendly Hotels in Rock Hall
- Romantic Hotels in Rock Hall
- Hotels with an Outdoor Pool in Rock Hall
- Hotels with Free Breakfast in Rock Hall
- Motels in Rock Hall
- Cheap Hotels in Rock Hall
- Beach Hotels in Rock Hall
- 5 Star Hotels in Rock Hall
- Family Hotels in Rock Hall
- Hotels with Hot Tubs in Rock Hall
- Business Hotels in Rock Hall
- Guest Houses in Rock Hall
- Cottages in Rock Hall
- Apartments in Rock Hall
- Hotels near The Mainstay
- Hotels near Betterton Beach
- Hotels near Rock Hall Harbor
- Hotels near Waterman’s Museum
- Washington College
- River Arts Chestertown
- Historical Society of Kent County Maryland
- Garfield Center for the Arts at the Prince Theater
- Wilmer Park
- Rolphs Wharf Marina
- Worton Vacations
- Visit Worton
- Visit Church Hill
- Cassinelli Winery and Vineyards
- Visit Kennedyville
- Visit Still Pond
- Visit Great Oak Landing
- Visit Crumpton
- Visit Betterton
- Visit Rock Hall
- Rock Hall Vacations
- The Mainstay
- Rock Hall Harbor
- Waterman’s Museum
- Car rentals near Worton
- Car rentals near Pomona
- Car rentals near Fairlee
- Car rentals near Georgetown
- Car rentals near Church Hill
- Car rentals near Great Oak Landing
- Car rentals near Crumpton
- Car rentals near Crumpton Auction
- Car rentals near Edesville
- Car rentals near Tolchester Beach
- Car rentals near Price
- Car rentals near Betterton
- Car rentals near Rock Hall
- Avis Rental Cars in Rock Hall
