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Search Guest Houses in Chestertown

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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

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

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
Beach

Top Floor East Handicap Accessible

2.0 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Mar - 7 Mar
Top Floor East Handicap Accessible
Second Floor Standard Deluxe Bay View
Beach

Second Floor Standard Deluxe Bay View

2.0 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
7 Mar - 8 Mar
Second Floor Standard Deluxe Bay View
Second Floor East Standard Deluxe
Beach

Second Floor East Standard Deluxe

2.0 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Mar - 7 Mar
Second Floor East Standard Deluxe
Center Parlor Room at Sandy Cove
Beach

Center Parlor Room at Sandy Cove

2.5 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
9 Mar - 10 Mar
Center Parlor Room at Sandy Cove
First Floor Family Deluxe Suite
Beach

First Floor Family Deluxe Suite

2.5 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Mar - 7 Mar
First Floor Family Deluxe Suite
Top Floor Standard Suite
Beach

Top Floor Standard Suite

2.0 star property
The price is AED 1,186
AED 1,724 total
includes taxes & fees
9 Mar - 10 Mar
Top Floor Standard Suite
Top Floor Standard Deluxe
Beach

Top Floor Standard Deluxe

2.5 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
9 Mar - 10 Mar
Top Floor Standard Deluxe
Second Floor Standard Suite Bay View
Beach

Second Floor Standard Suite Bay View

2.0 star property
The price is AED 1,279
AED 1,823 total
includes taxes & fees
9 Mar - 10 Mar
Second Floor Standard Suite Bay View
Top Floor Deluxe Suite Bay View
Beach

Top Floor Deluxe Suite Bay View

2.5 star property
The price is AED 1,349
AED 1,897 total
includes taxes & fees
9 Mar - 10 Mar
Top Floor Deluxe Suite Bay View
Second Floor Family Deluxe
Beach

Second Floor Family Deluxe

2.0 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Mar - 7 Mar
Second Floor Family Deluxe
Top Floor Family Deluxe Bay View
Beach

Top Floor Family Deluxe Bay View

2.0 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
6 Mar - 7 Mar
Top Floor Family Deluxe Bay View
First Floor Bay View Deluxe Suite
Beach

First Floor Bay View Deluxe Suite

2.0 star property
The price is AED 1,349
AED 1,897 total
includes taxes & fees
7 Mar - 8 Mar
First Floor Bay View Deluxe Suite
Top Floor Family Deluxe
Beach

Top Floor Family Deluxe

2.5 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Mar - 7 Mar
Top Floor Family Deluxe
Top Floor Handicap Accessible Bay View
Beach

Top Floor Handicap Accessible Bay View

2.0 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
6 Mar - 7 Mar
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.
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Other property types in Chestertown

First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is AED 360
AED 579 total
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown
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.

9.4 out of 10, Exceptional, (22)
"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.
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (256)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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.