Riverfront Retreat, a spacious home on the Eastern Shore, offers a relaxing getaway for families. With two main floor bedrooms and four upstairs bedrooms with private bathrooms, there's room to spread out. Enjoy meals in the combination living/dining room or outside on the deck overlooking the river.
Reviews
9.89.8 out of 10
Exceptional
Entire home
6 bedrooms6 bathroomsSleeps 14
Popular amenities
Kitchen
Washer
Dryer
Air conditioning
Outdoor Space
Parking available
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
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!
Property amenities
Beach
Beach towels
Internet
Available in the house: WiFi
Parking and transportation
Limited onsite parking (max 6 spaces)
Onsite parking options include a garage
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Ice maker
Microwave
Oven
Paper towels
Refrigerator
Stovetop
Toaster
Dining
Dining table
Bedrooms
6 bedrooms
Bedsheets provided
Bathroom
6 private bathrooms
Bathtub or shower
Hair dryer
Jetted bathtub
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Separate dining area
Entertainment
Games
Smart TV with cable/satellite channels
Outdoor areas
Balcony
Barbecue grill
Firepit
Garden
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Ceiling fan
Heating
Pets
No pets allowed
Suitability/Accessibility
Hardwood flooring in public areas
Smoking not allowed
Services and conveniences
Phone
Safe
Location highlights
In the city center
Near a hospital
Near the marina
On a river
On the waterfront
Things to do
Arcade/game room
Bicycles
Billiards/pool table
Kayak
Birdwatching nearby
Cycling nearby
Fishing nearby
Golfing nearby
Kayaking nearby
Motor boating nearby
Swimming nearby
Wildlife walks nearby
Safety features
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)
General
Bicycles
Garden
Similar properties
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Chestertown
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
There is a maximum of six vehicles to be parked at/on/nearby our home.
Pets
Pets not allowed
Children and extra beds
Children are welcome
Note from host: Waterfront is a small sand beach, 100' from house.
Events
No events allowed
Larger events are welcome, at an additional charge
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Note from host: Larger events are welcome, at an additional charge
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the neighborhood
Located in Chestertown, this vacation home is in the city center and on the waterfront. Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights, and some of the area's attractions include Larrabee Arts Center and Crumpton Auction. Kayaking, motor boating, and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Chestertown travel guide
Garfield Center for the Arts at the Prince Theater
8 min walk - 0.7 km
River Arts Chestertown
8 min walk - 0.7 km
Chestertown Historic District
9 min walk - 0.8 km
Getting around
Baltimore, MD (MTN-Martin State)
104 min drive
Restaurants
Milano's Pizzeria
4 min drive
McDonald's
3 min drive
Dunkin
3 min drive
Royal Farms
3 min drive
Procolino's
3 min drive
Frequently asked questions
Is Beautiful, spacious waterfront home, an easy walk to historic Chestertown pet-friendly?
No, pets are not allowed at this property.
How much is parking?
Limited spots are available.
What time is check-in at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?
Check-in begins at 4:00 PM.
What time is check-out at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?
Check-out is at 10:00 AM.
Where is Beautiful, spacious waterfront home, an easy walk to historic Chestertown located?
Located in the heart of Chestertown, this vacation home is within a 10-minute walk of Historical Society of Kent County Maryland, Chestertown Historic District, and Garfield Center for the Arts at the Prince Theater. Washington College and Sumner Hall are also within 10 minutes.
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Beautiful, spacious waterfront home, an easy walk to historic Chestertown Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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
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.
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.
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.
Stayed 5 nights in Oct 2025
Verified
8/10 Good
Janise F.
24 August 2023
Liked: Check-in, location, listing accuracy
Disliked: Communication
Bridgeway Community Church
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.
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!
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!
My family and I enjoyed our stay in Chestertown. It was 11 of us… 9 adults and 2 teenagers (13 &15). The house with all the gorgeous views were so relaxing and peaceful. The house was spotless. We did early morning walks throughout the town and stopped at Evergrain bakery for bread and cinnamon rolls. Some days we rode the bicycles and that was fun. Everything was easy to find and the property manager was very helpful. Lovely house, lovely town, lovely people and a lovely stay!
We’ll appointed and equipped house for a real Chester River experience. Access to the River and walkable to Chestertown makes this a special place to stay.
We enjoyed the property very much. It is a spacious home with beautiful views and great backyard. It is an easy walk to the downtown in a very pretty neighborhood.
The house fits many people and all the rooms are big and very comfortable.
It was a fun time with my family!
We were a group of 3 families with kids ranging in age from 3 to 8. We had such a wonderful time at the River Retreat. The space is great for a large group, the "bunk room" perfect for kids who want to bunk together, and the river views, kayaks, and short walk to town make it perfect. Thank you!
It is a very spacious beautiful house. Many indoor and outdoor toys to keep us entertained. Great responses when we needed to communicate. Lovely neighborhood and within walking to town. Only disappointment was how shallow the water at the dock was during low tide. We ended up renting a slip at the Chestertown marina which was close by so our boat trips were not limited by the tide.
Thanks so much for a wonderful home base for our extended family vacation. The house was perfect for us - clean, spacious, great location and management was easy to work with. We will be back!
My family and I thoroughly enjoyed our stay in Chestertown. The house is amazing and the views were breathtaking. It was nice to have the dock where we could keep our boat. We look forward to coming again in the future.
The home was impressive with a lot of room for our multiple families to stay. Large kitchen, dinning and bedroom areas. We enjoyed the ability to take the Kayaks out on the water, walking downtown for ice cream and bake goods. We enjoy Chestertown with this being our second stay in the area. We will be back I am sure.
This home exceeded our expectations in every way. The property was exceptionally clean and well maintained. We enjoyed the water views and kayaks and exploring the nearby town on foot and on bikes. We rented the home for a special celebration and we are very happy with our stay.
Very cool house with all the amenities we needed for a great long weekend stay. Loved the view in the morning with coffee and house had so many areas to relax in. Screened porch in basement was really nice and loved the billiard room. It was also really cool that it is just a short walk to lots of shops and restaurants. There were several unexpected surprises like a firepit and commercial ice maker that were nice to have. Would definitely stay here again in the future.
Had an awesome weekend in the middle of winter with my husband. Can't wait to bring our whole family this summer. Highly recommend, definitely want to go back!