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
Compare 16 Guest Houses in Chestertown with updated reviews, rates, and availability.

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, (186)

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 AED 1,233
AED 1,774 total
includes taxes & fees
20 May - 21 May

Center Parlor Room at Sandy Cove
Center Parlor Room at Sandy Cove
The price is AED 1,326
AED 1,872 total
includes taxes & fees
22 May - 23 May

First Floor Bay View Deluxe Suite
First Floor Bay View Deluxe Suite
The price is AED 1,465
AED 2,020 total
includes taxes & fees
20 May - 21 May

Top Floor Deluxe Suite Bay View
Top Floor Deluxe Suite Bay View
The price is AED 1,465
AED 2,020 total
includes taxes & fees
26 May - 27 May

Top Floor Handicap Accessible Bay View
Top Floor Handicap Accessible Bay View
The price is AED 1,326
AED 1,872 total
includes taxes & fees
19 May - 20 May

First Floor Family Deluxe Suite
First Floor Family Deluxe Suite
The price is AED 1,233
AED 1,774 total
includes taxes & fees
20 May - 21 May
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

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (1)

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, (217)

BAYSIDE BUNGALOW
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (35)
The price is AED 735
AED 1,098 total
includes taxes & fees
18 May - 19 May
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

Home2 Suites by Hilton Baltimore/White Marsh
5/5 Excellent
"The studio was very clean, very nice however we were in the second floor and can hear the music from the lobby, all night lo g"
A verified traveler stayed at Home2 Suites by Hilton Baltimore/White Marsh
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
- Farmstay in Chestertown
- Condo Rentals in Chestertown
- Cabin Rentals in Chestertown
- Villas in Chestertown
- Lodges in Chestertown
- Hotels