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

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Exterior
Exterior
Miscellaneous
Exterior
Main entrance, circular driveway

Reviews

9.8 out of 10
Exceptional
6 bedrooms5+ bathroomsSleeps 14

Popular amenities

  • Kitchen
  • Dryer
  • Barbecue grill
  • Washer
  • Outdoor space
  • Parking available

Explore the area

Map
Chestertown, MD
  • Historical Society of Kent County Maryland
    ‪6 min walk‬
  • Washington College
    ‪8 min walk‬
  • River Arts Chestertown
    ‪11 min walk‬
  • Aberdeen, MD (APG-Phillips Army Airfield)
    ‪91 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

Duck Bedroom

1 Queen Bed

Green Bedroom

1 Queen Bed

Library Bedroom

1 Queen Bed

Map Bedroom

2 Single Beds

Master Bedroom Suite

1 King Bed

White Bedroom

+1
4 Single Beds and 1 Queen Bed

5 bathrooms, 2 half bathrooms

Green Bathroom

Bathtub or shower · Toilet

Ground floor bathroom

Bathtub or shower · Toilet

Jack-n-Jill

Bathtub or shower · Toilet

Main Hall Bathroom

Toilet

Map Bathroom

Bathtub or shower · Toilet

Master Bathroom

Toilet · Shower only · Jetted bathtub

Side Hall Bathroom

Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

About this property

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
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Waterfront is a small sand beach, 100' from house.
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Events

No events allowed
Larger events are welcome, at an additional charge
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Pets

No pets allowed
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Smoking

Smoking is not permitted
There is a maximum of six vehicles to be parked at/on/nearby our home.

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
On-site 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

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre 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 Crumpton Auction and Hazel Miner Monument. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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?

Checkout 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 holiday home is within a 10-minute walk of Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Washington College. River Arts Chestertown and Wilmer Park are also within 15 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

10/10

Check-in

9.4/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

8/10 Good

Harold L.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Family Vacation

We had a great time
Stayed 5 nights in Aug 2024

10/10 Excellent

David K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

sandra l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Thomas H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

10/10 Excellent

Helen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Janise F., Columbia, Maryland

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.
Stayed 6 nights in Aug 2023

10/10 Excellent

Maggie E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

Great Weekend

Fantastic spot for a great weekend!!!
Stayed 3 nights in Sep 2021

10/10 Excellent

Tara R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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!

About the host

Hosted by Diane Oliver

Host profile image
We are a family of seven, from suburban Philadelphia. We were introduced to Chestertown about seven years ago, by dear friends who've been on the river for 15 years+. It didn't take long for us to fall in love with Chestertown and being on the water here. This is our first opportunity to have a waterfront property, and we are excited to share it.

Why they chose this property

This property is great - the home is spacious and nice. The pier gives great access to the river (the water is very shallow at low tide). And it is an easy walk into historic Chestertown - for the Saturday morning farmer's market, to go to Evergrain Bakery (their sunbuns are outstanding) (its closed Monday and Tuesday), Play it Again Sam (excellent breakfast sandwiches), or 98 Cannon (waterfront dining).

What makes this property unique

It is a special place - views of the river from the LR/DR, breakfast room, main kitchen, MBR sitting room, two of the second floor/upstairs bedrooms, and the ground floor great room. The screened-in-porch on the ground floor and the deck off the main floor (accessible from the breakfast room, LR/DR, and MBR sitting room) also give great views of the water. And the lighted pier provides water access and it looks beautiful from the house, day and night.

Languages:

English

Premier Host

They consistently provide great experiences for their guests