Photo by Assya A
Search Guest Houses 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 Guest Houses in Chestertown
Compare 15 Guest Houses in Chestertown with updated reviews, rates, and availability.
Calico Cottage Guest House
Calico Cottage Guest House
10.0 out of 10, Exceptional, (8)
Top Floor East Handicap Accessible
Top Floor East Handicap Accessible
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Center Parlor Room at Sandy Cove
Center Parlor Room at Sandy Cove
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor Standard Deluxe Bay View
Second Floor Standard Deluxe Bay View
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor East Standard Deluxe
Second Floor East Standard Deluxe
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor Standard Suite Bay View
Second Floor Standard Suite Bay View
The price is SAR 1,308
SAR 1,864 total
includes taxes & fees
9 Jan - 10 January 2025
First Floor Bay View Deluxe Suite
First Floor Bay View Deluxe Suite
The price is SAR 1,380
SAR 1,940 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor Handicap Accessible Bay View
Top Floor Handicap Accessible Bay View
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
16 Jan - 17 January 2025
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 Guest Houses in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Apartments in Chestertown
- Cottages 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