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Search Guest Houses in Chestertown

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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

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

Island Life! Kent Island Waterfront with Pool-Bring your boat!
3 bedrooms, iron/ironing board, travel crib, free WiFi

Island Life! Kent Island Waterfront with Pool-Bring your boat!

10.0 out of 10, Exceptional, (186)
"The place was very clean , had all the things in the home to make your stay wonderful!!!! Kitchen stocked with cooking equipment, towels for the pool, and the was owner was a great host."
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Calico Cottage Guest House
Terrace/patio

Calico Cottage Guest House

10.0 out of 10, Exceptional, (8)
"This tiny house is tastefully furnished and, coupled with the quiet neighborhood, provides a relaxing, peaceful environment."
Calico Cottage Guest House
Top Floor East Handicap Accessible
Miscellaneous

Top Floor East Handicap Accessible

2.0 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May
Top Floor East Handicap Accessible
Center Parlor Room at Sandy Cove
Miscellaneous

Center Parlor Room at Sandy Cove

2.5 star property
The price is AED 1,326
AED 1,872 total
includes taxes & fees
15 May - 16 May
Center Parlor Room at Sandy Cove
First Floor Bay View Deluxe Suite
Miscellaneous

First Floor Bay View Deluxe Suite

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

Top Floor Deluxe Suite Bay View

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

Top Floor Handicap Accessible Bay View

2.0 star property
The price is AED 1,326
AED 1,872 total
includes taxes & fees
14 May - 15 May
Top Floor Handicap Accessible Bay View
First Floor Family Deluxe Suite
Miscellaneous

First Floor Family Deluxe Suite

2.5 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May
First Floor Family Deluxe Suite
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.5 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May
Top Floor Standard Deluxe
Second Floor Standard Deluxe Bay View
Miscellaneous

Second Floor Standard Deluxe Bay View

2.0 star property
The price is AED 1,326
AED 1,872 total
includes taxes & fees
13 May - 14 May
Second Floor Standard Deluxe Bay View
Second Floor East Standard Deluxe
Miscellaneous

Second Floor East Standard Deluxe

2.0 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
13 May - 14 May
Second Floor East Standard Deluxe
Top Floor Family Deluxe Bay View
Miscellaneous

Top Floor Family Deluxe Bay View

2.0 star property
The price is AED 1,326
AED 1,872 total
includes taxes & fees
20 May - 21 May
Top Floor Family Deluxe Bay View
Top Floor Family Deluxe
Miscellaneous

Top Floor Family Deluxe

2.5 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
20 May - 21 May
Top Floor Family Deluxe
Second Floor Standard Suite Bay View
Miscellaneous

Second Floor Standard Suite Bay View

2.0 star property
The price is AED 1,395
AED 1,946 total
includes taxes & fees
20 May - 21 May
Second Floor Standard Suite Bay View
Top Floor Standard Suite
Miscellaneous

Top Floor Standard Suite

2.0 star property
The price is AED 1,302
AED 1,848 total
includes taxes & fees
20 May - 21 May
Top Floor Standard Suite
Second Floor Family Deluxe
Miscellaneous

Second Floor Family Deluxe

2.0 star property
The price is AED 1,233
AED 1,774 total
includes taxes & fees
20 May - 21 May
Second Floor Family Deluxe
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.
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Other property types in Chestertown

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (215)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (35)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is AED 643
AED 1,001 total
includes taxes & fees
13 May - 14 May
BAYSIDE BUNGALOW
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.