Entire home

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

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Exterior
Interior
Fridge, microwave, oven, stovetop
Smart TV
Property grounds

Reviews

9.8 out of 10

Exceptional

Entire home

6 bedrooms6 bathroomsSleeps 14

Popular amenities

  • Washer
  • Barbecue grill
  • Outdoor Space
  • Parking available
  • Air conditioning
  • Kitchen

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 manager

Diane Oliver

Languages

English

Property amenities

Beach

  • Beach towels

Internet

  • WiFi available

Parking and transportation

  • Limited onsite parking (max 6 spaces)
  • Onsite parking options include a garage
  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Cookware/dishes/utensils
  • Electric kettle
  • Ice maker
  • Paper towels

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bed sheets provided

Bathrooms

  • 6 bathrooms
  • Bathtub or shower
  • Jetted bathtub
  • Towels provided
  • Hair dryer
  • Toilet paper
  • Soap
  • Shampoo

Living spaces

  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service
  • Pool or billiards table
  • Arcade/game room
  • Games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Hardwood flooring in public areas
  • Smoke-free property

Services and conveniences

  • Safe
  • Phone

Location highlights

  • On the river
  • On the waterfront
  • In the city center
  • Near a hospital

Things to do

  • Bicycle on site
  • Kayak on site
  • Marina nearby
  • Golf nearby
  • Fishing nearby
  • Kayaking nearby
  • Cycling nearby
  • Wildlife and game walks nearby
  • Birdwatching nearby
  • Swimming nearby
  • Power boating 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)

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Waterfront is a small sand beach, 100' from house.

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

Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 6 min walk - 0.5 km
  • Garfield Center for the Arts at the Prince Theater - 7 min walk - 0.6 km
  • Washington College - 8 min walk - 0.7 km
  • River Arts Chestertown - 11 min walk - 1.0 km
  • Rolphs Wharf Marina - 10 min drive - 7.6 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Dining Hall - ‬17 min walk
  • ‪Procolino Pizza - ‬3 min drive
  • ‪China House - ‬3 min drive
  • ‪The Freeze - ‬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 at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

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 0.4 mi (0.6 km) from Washington College and within 16 mi (25 km) of Betterton Beach and Rock Hall Harbor. Queenstown Premium Outlets and Queenstown Harbor Golf Club are also within 25 mi (40 km).

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 19 out of 22 reviews" "
Rating 8 - Good. 3 out of 22 reviews" "
Rating 6 - Okay. 0 out of 22 reviews" "
Rating 4 - Poor. 0 out of 22 reviews" "
Rating 2 - Terrible. 0 out of 22 reviews" "

9.6/10

Cleanliness

Reviews

10/10 Excellent

David K.

Liked: Cleanliness
Awesome stay on the Chester River
Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!
Stayed 5 nights in Sep 2024

8/10 Good

Harold L.

Liked: Cleanliness
Family Vacation
We had a great time
Stayed 5 nights in Aug 2024

10/10 Excellent

Thomas H.

Liked: Cleanliness
Looking for the perfect getaway? This is it!
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.
Stayed 7 nights in Jul 2024

8/10 Good

Janise F., Columbia, Maryland

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.
Stayed 6 nights in Aug 2023

10/10 Excellent

Helen C.

Liked: Cleanliness
Family reunion
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.
Stayed 21 nights in Jul 2023

10/10 Excellent

sandra l.

Liked: Cleanliness
Great House
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
Stayed 4 nights in Jul 2023

10/10 Excellent

Maggie E.

Liked: Cleanliness
Great stay on the water for family and friends!
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!
Stayed 4 nights in May 2023

10/10 Excellent

Tony P.

Liked: Cleanliness
Excellent House!
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!
Stayed 6 nights in Aug 2022

10/10 Excellent

Michael K.

Liked: Cleanliness
Great house for a relaxing family and friends get-together
Rental process was very easy
Stayed 4 nights in Jul 2022

10/10 Excellent

Marilyn O.

Liked: Cleanliness
Relax at River in Chestertown
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!
Stayed 7 nights in Jul 2022

10/10 Excellent

Kate s.

Liked: Cleanliness
Great place for a family gathering!
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.
Stayed 4 nights in Jun 2022

8/10 Good

Ivonne R., Jacksonville, Florida

Liked: Cleanliness
Family Wedding Weekend
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!
Stayed 3 nights in Oct 2021

10/10 Excellent

Wayne C.

Liked: Cleanliness
Great Weekend
Fantastic spot for a great weekend!!!
Stayed 3 nights in Sep 2021

10/10 Excellent

Tara R.

Liked: Cleanliness
Wonderful Stay in Chestertown
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!
Stayed 2 nights in Sep 2021

10/10 Excellent

Diane R.

Liked: Cleanliness
Beautiful house and property
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.
Stayed 7 nights in Aug 2021

10/10 Excellent

Loren G.

Liked: Cleanliness
Family Fun
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!
Stayed 7 nights in Jul 2021

10/10 Excellent

john s.

Liked: Cleanliness
Chestertown
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.
Stayed 6 nights in Jul 2021

10/10 Excellent

Lori J.

Liked: Cleanliness
Chestertown's Best
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.
Stayed 7 nights in Jul 2021

10/10 Excellent

Sara S.

Liked: Cleanliness
It was great, we had family members from age 3 to 83 and everyone enjoyed themselves.
So convenient would def recommend it.
Stayed 5 nights in Jun 2021

10/10 Excellent

Alyson O., Shelton, CT USA

Liked: Cleanliness
Amazing Home
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.
Stayed 4 nights in Jun 2021

10/10 Excellent

Keith P.

Liked: Cleanliness
Great long weekend 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.
Stayed 3 nights in Jun 2021

10/10 Excellent

Bethany C.

Liked: Cleanliness
Perfect location, incredible home
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!