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Search Guest Houses in Chestertown

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Check prices for these dates

Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb
In one month
28 Feb - 2 Mar
In two months
28 Mar - 30 Mar

Compare 15 Guest Houses in Chestertown with updated reviews, rates, and availability.

Calico Cottage Guest House
Outdoor dining

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 1,116
AED 1,650 total
includes taxes & fees
6 Feb - 7 Feb
Top Floor East Handicap Accessible
Second Floor Standard Deluxe Bay View
Miscellaneous

Second Floor Standard Deluxe Bay View

2.0 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
6 Feb - 7 Feb
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 1,116
AED 1,650 total
includes taxes & fees
6 Feb - 7 Feb
Second Floor East Standard Deluxe
Center Parlor Room at Sandy Cove
Miscellaneous

Center Parlor Room at Sandy Cove

2.5 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
6 Feb - 7 Feb
Center Parlor Room at Sandy Cove
First Floor Family Deluxe Suite
Miscellaneous

First Floor Family Deluxe Suite

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

Top Floor Standard Suite

2.0 star property
The price is AED 1,186
AED 1,724 total
includes taxes & fees
6 Feb - 7 Feb
Top Floor Standard Suite
Top Floor Standard Deluxe

Top Floor Standard Deluxe

2.5 star property
The price is AED 1,116
AED 1,650 total
includes taxes & fees
6 Feb - 7 Feb
Top Floor Standard Deluxe
Second Floor Standard Suite Bay View
Miscellaneous

Second Floor Standard Suite Bay View

2.0 star property
The price is AED 1,279
AED 1,823 total
includes taxes & fees
6 Feb - 7 Feb
Second Floor Standard Suite Bay View
Top Floor Deluxe Suite Bay View
Miscellaneous

Top Floor Deluxe Suite Bay View

2.5 star property
The price is AED 1,349
AED 1,897 total
includes taxes & fees
6 Feb - 7 Feb
Top Floor Deluxe Suite Bay View
Second Floor Family Deluxe
Property grounds

Second Floor Family Deluxe

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

Top Floor Family Deluxe Bay View

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

First Floor Bay View Deluxe Suite

2.0 star property
The price is AED 1,349
AED 1,897 total
includes taxes & fees
13 Feb - 14 Feb
First Floor Bay View Deluxe Suite
Top Floor Family Deluxe
Miscellaneous

Top Floor Family Deluxe

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

Top Floor Handicap Accessible Bay View

2.0 star property
The price is AED 1,209
AED 1,749 total
includes taxes & fees
13 Feb - 14 Feb
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

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Terrace/patio

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Private rear courtyard

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

10.0 out of 10, Exceptional, (206)
"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!
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.