Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Top rated by guests
Exterior
Chefs kitchen with breakfast table and bar stools..  Room for all.
Interior
Living area
Exterior
review stars
9.8Outstanding
(23 Ratings)
"The property is in a great location and beautiful setting. We had group from college celebrating a commitment party of our college friends"
Mary Kay B.
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(23 Ratings)

House in Chestertown, MD

14 guests · 6 bedrooms · 6 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in 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

Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best of the Eastern Shore. With two main floor bedrooms, including a master suite accompanied with sitting room with full river views. The second main floor bedroom, our Library Bedroom, is spacious and features hardwood floors and built in bookcases. The four large bedrooms on the second floor provide plenty of room to spread out and enjoy. Two of the upstairs bedrooms have their own bathroom, and a jack-n-jill bathroom serves the other two bedrooms.

The main floor living areas are equally built to please - the 33X24 combination LR/DR with hardwood floors and a cathedral ceiling is a great spot for family meals around the 14 person dinner table, and for games, all while looking out at the river. Get closer to the river on the deck, which receives mid-day sun, as well as shade from the large Magnolia adjacent to our home.

The main floor kitchen is fully equipped with a large center island, breakfast dining area, and another set of breathtaking views of the river. The ground floor features a great room with pool table, 75 inch television, and views of the river.

Prefer to eat outside? The ground floor also includes a substantial screened-in-porch, complete with two ceiling fans, as well as a table with seating for eight that is ready for you.

Beyond the many attributes of the house itself, the property features a 110 foot private pier, which is great for launching the kayaks that are provided for your enjoyment (4 single, one double), the paddleboard, swimming, and there is a mooring at your disposal if you want to bring your power boat.

All of this, and you are about a four block walk to historic Chestertown.

We purchased the home in November 2020 from the original (1989) owners, and we love this place! In early 2021 the main entry, LR/DR, MBR, Library bedroom, and all upstairs bedrooms were freshly painted and updated. The furniture in the LR/DR and breakfast room is fresh too. Likewise, the furniture on the ground floor, in the great room and the screened-in porch is all fresh. The pool table in the ground floor great room is a classic, which we purchased from a Chestertown resident, and we had it re-felted in the spring of 2021.

The main floor, primary kitchen is spacious and has served us as a wonderful gathering place, and it has original appliances including an electric stove. The ground floor, secondary kitchen is smaller and functional.

Our home is in a wonderful residential neighborhood. Most of our neighbors live in Chestertown year-round. It is important to us to be good neighbors, and so we aim to rent our home to people who want to use it for relaxing, fun vacation getaways - people who will use our home the same way we do. We want and need to be sure that our renters respect our neighbors and avoid any disruptive behavior - things like loud music, other excessive noise, or bright lights, particularly after hours. Likewise, parking is limited to six vehicles, which need to be kept on one of the two driveways. If you are looking for a beautiful home in a great area, with plenty of fun things to do, please come to our River Retreat!

Amenities at Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Non-smoking
No pets allowed

Map of Chestertown, MD


Ratings and reviews

9.8 / 10
Outstanding(23 Ratings)
10 / 10Outstanding·Oct 2025
The property is in a great location and beautiful setting. We had group from college celebrating a commitment party of our college friends
10 / 10Outstanding·Sep 2024
Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!
8 / 10Excellent·Aug 2024
We had a great time
10 / 10Outstanding·Jul 2024
The property was ideal for a family vacation. Despite the hot weather outside the property inside provided comfortable and spacious surroundings with a magnificent view of the river. It is close to the center of the town of Chesterfield with many shops, restaurants, and historical buildings within s short walking distance. The people of the town are most engaging-helping to make the stay memorable. A very special home in a very special place.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Beautiful, spacious waterfront home, an easy walk to historic Chestertown. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Beautiful, spacious waterfront home, an easy walk to historic Chestertown pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

We found 2 amenities for this rental. This includes non-smoking, and no pets allowed.