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

Chestertown, Maryland
$1416 avg/night
Bed 6

Bed

Bath 6

Bath

Home Private Vacation Home

Property Type

Sleep 14

Max Sleeps

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 havetheir 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!

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Limited Onsite Parking (max 6 Spaces) Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden Outdoor Furniture
  • BATHROOMS

    6 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Cycling Nearby Fishing Nearby Golf Nearby Kayak On Site Kayaking Nearby Marina Nearby Power Boating Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Arcade/game Room Games Pool Or Billiards Table Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Ceiling Fan Heating
  • LOCATION HIGHLIGHTS

    In The City Center Near A Hospital On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Phone Safe
  • SUITABILITY/ACCESSIBILITY

    Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 14

Map Map

School District Rates & Availability

Review Review

  • Mary Kay B.

    Submitted Oct 6, 2025

    Stayed Oct 1, 2025

    The property is in a great location and beautiful setting. We had group from college celebrating a commitment party of our college friends

  • David K.

    Submitted Sep 23, 2024

    Stayed Sep 18, 2024

    Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!

  • Harold L.

    Submitted Aug 6, 2024

    Stayed Aug 1, 2024

    We had a great time

  • Thomas H.

    Submitted Jul 20, 2024

    Stayed Jul 13, 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.

  • Janise F.

    Submitted Aug 24, 2023

    Stayed Aug 13, 2023

    This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the items but the ice maker were fixed.

  • Helen C.

    Submitted Jul 27, 2023

    Stayed Jul 1, 2023

    The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and beach and walking to Chestertown.

  • sandra l.

    Submitted Jul 27, 2023

    Stayed Jul 22, 2023

    The whole family enjoyed this beautiful house. We also enjoyed the convenience of the dock right outside the backyard. The short walk into town was also nice

  • Maggie E.

    Submitted May 17, 2023

    Stayed May 11, 2023

    This property is huge and has everything you need to enjoy a waterfront vacation. We stayed with a group that was in town for a wedding. A beautiful quiet neighborhood within walking distance to everything in charming Chestertown. It was also great to have access to the kayaks and get on the water! The house was very clean but could benefit from some repairs. The deck needs to be redone and wasn’t as nice as the rest of the house. Especially the deck railing which was unstable, so we kept the kids away from it. Quite a few windows were inoperable due to the visible foundation issues. Additional seating on the deck and in the yard, extra pillows and blankets would have been nice, but overall would recommend this lovely waterfront home!

  • Tony P.

    Submitted Aug 31, 2022

    Stayed Aug 14, 2022

    The house was everything we could have hoped for. Great location, plenty of space, clean, and spectacular views. We've already booked it for next year!

  • Michael K.

    Submitted Aug 6, 2022

    Stayed Jul 22, 2022

    Rental process was very easy

Your dates are Available!

Total

Includes taxes and fees
$1,416+
View details