Photo by Assya A
Search Guest Houses in Chestertown
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Guest Houses in Chestertown
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Island Life! Kent Island Waterfront with Pool-Bring your boat!
10.0 out of 10, Exceptional, (193)
Top Floor Family Deluxe Bay View
Top Floor Family Deluxe Bay View
Calico Cottage Guest House
Calico Cottage Guest House
10.0 out of 10, Exceptional, (8)
Second Floor East Standard Deluxe
Second Floor East Standard Deluxe
Second Floor Standard Suite Bay View
Second Floor Standard Suite Bay View
Top Floor Standard Suite
Top Floor Standard Suite
Second Floor Family Deluxe
Second Floor Family Deluxe
Top Floor Handicap Accessible Bay View
Top Floor Handicap Accessible Bay View
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
Top Chestertown Hotel Reviews
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
10/10 Excellent
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Guest Houses in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Apartments in Chestertown
- Cottages in Chestertown
- Motels in Chestertown
- Houseboats in Chestertown
- RV Parks in Chestertown
- B&B in Chestertown
- Farmstay in Chestertown
- Condo Rentals in Chestertown
- Villas in Chestertown
- Cabin Rentals in Chestertown
- Lodges in Chestertown
- Hotels