Photo by Julie Miller
Search Inns in Chestertown
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Inns in Chestertown
Compare 2 Inns in Chestertown with updated reviews, rates, and availability.
The Inn at Erlowest
The Inn at Erlowest
9.6 out of 10, Exceptional, (183)
Top of the World Resort
Top of the World Resort
8.2 out of 10, Very Good, (12)
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
Peaceful Lakeside Retreat with Private Beach
Peaceful Lakeside Retreat with Private Beach
9.2 out of 10, Wonderful, (17)
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Cozy retreat with fireplace, kayaks, and shared beach/pond access
9.0 out of 10, Wonderful, (16)
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, (53)
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
"Fun"
A verified traveler stayed at Six Flags Lodge & Indoor Waterpark
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Inns in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Cabin Rentals in Chestertown
- Cottages in Chestertown
- Apartments in Chestertown
- Motels in Chestertown
- Chalets in Chestertown
- Condo Rentals in Chestertown
- Lodges in Chestertown
- Farmstay in Chestertown
- Castles in Chestertown
- B&B in Chestertown
- RV Parks in Chestertown
- Resorts in Chestertown
- Villas in Chestertown
- Aparthotels in Chestertown
- Guest Houses in Chestertown
- Holiday Park Resorts in Chestertown
- Hotels