House in Chestertown, MD
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boat & dock at our deep water pier. Crabbing* (trap & net), fishing (2 rods), & biking (4 provided) are also fun activities to enjoy here at the property. Fire pit (all seasons), indoor fireplace, and outdoor hot tub (available October through the end of April). We will do our best to keep hot tub in working order, but cannot guarantee it will be in working condition 100% of the time. It does take longer to get technicians out here. However we will do our best. We look forward to your stay. All are welcome.
*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.
*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.
Amenities at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Non-smoking
No pets allowed
Family friendly
Map of Chestertown, MD
Ratings and reviews
Summary of reviewsGuests loved the well-furnished house with outdoor seating, a huge screened-in porch by the river, spacious bedrooms, and a well-stocked kitchen. The host, Beth, was responsive and accommodating. Highly recommended for a relaxing vacation!
10 / 10Outstanding·May 2026
We had a wonderful stay in Chestertown. The house was really nice, and we loved the outdoor area. Kitchen has everything we needed. The parking was plentiful.
10 / 10Outstanding·May 2026
The whole house was totally equipped with everything we needed although we brought everything for bathrooms and kitchen….it was already provided from shampoo/conditioner, body wash and hand soap in all bathrooms. Ziplock bags and foil in kitchen. We did buy birdseed for the feeders in the yard and then found a metal can on back porch with it so we added our leftovers. Hostess was very good with communication. The location of the home is outstanding being right on the river. If we ever come back to the area, we would love to stay here again!
10 / 10Outstanding·Apr 2026
This was the perfect house for a beautiful Chestertown weekend. The host was quick to respond and the house itself was even better than expected!
10 / 10Outstanding·Apr 2026
Always love staying here.
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Top rated by guests
10Outstanding
(111 Ratings)
Guests loved the well-furnished house with outdoor seating, a huge screened-in porch by the river, spacious bedrooms, and a well-stocked kitchen. The host, Beth, was responsive and accommodating. Highly recommended for a relaxing vacation!
From real guest reviews summarized by AIDon't miss out! Price and availability may change
