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Search Guest Houses in Chestertown

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

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

2.0 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor East Handicap Accessible

Center Parlor Room at Sandy Cove

2.5 star property
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
9 Jan - 10 January 2025
Center Parlor Room at Sandy Cove

Second Floor Standard Deluxe Bay View

2.0 star property
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 East Standard Deluxe

2.0 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor East Standard Deluxe

Second Floor Standard Suite Bay View

2.0 star property
The price is SAR 1,308
SAR 1,864 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor Standard Suite Bay View

First Floor Bay View Deluxe Suite

2.0 star property
The price is SAR 1,380
SAR 1,940 total
includes taxes & fees
9 Jan - 10 January 2025
First Floor Bay View Deluxe Suite

Top Floor Handicap Accessible Bay View

2.0 star property
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
16 Jan - 17 January 2025
Top Floor Handicap Accessible Bay View

Top Floor Standard Suite

2.0 star property
The price is SAR 1,213
SAR 1,764 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor Standard Suite

Second Floor Family Deluxe

2.0 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Second Floor Family Deluxe

First Floor Family Deluxe Suite

2.5 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
First Floor Family Deluxe Suite

Top Floor Standard Deluxe

2.5 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor Standard Deluxe

Top Floor Deluxe Suite Bay View

2.5 star property
The price is SAR 1,380
SAR 1,940 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor Deluxe Suite Bay View

Top Floor Family Deluxe Bay View

2.0 star property
The price is SAR 1,237
SAR 1,789 total
includes taxes & fees
9 Jan - 10 January 2025
Top Floor Family Deluxe Bay View

Top Floor Family Deluxe

2.5 star property
The price is SAR 1,142
SAR 1,688 total
includes taxes & fees
9 Jan - 10 January 2025
Top 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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

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

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (23)
"Fifteen ladies from my church stayed at this Vrbo for a weekend conference in Annapolis. We enjoyed the property and the house! We had a beautiful weekend and even got on the water, played pickle ball, and enjoyed the views. The house is beautiful! The kitchen is well stocked and the house is comfortable and there is plenty of parking. Since it was November, the heated sunroom floors were a wonderful bonus. Thank you for the memories and a wonderful stay!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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.