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

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Property grounds
Exterior
Exterior
Main entrance, circular driveway
Reviews
9.8 out of 10 Exceptional
6 bedrooms5+ bathroomsSleeps 14

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor space
  • Barbecue grill

Explore the area

Map
Chestertown, MD
  • Popular LocationWashington College8 min walk
  • Popular LocationRiver Arts Chestertown11 min walk
  • Popular LocationWilmer Park11 min walk
  • AirportSalisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)100 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

Languages

English

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Barbecue grill

House Rules

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

Children

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

Events

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

Pets

No pets allowed

Smoking

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

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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. Rolphs Wharf Marina and Rock Hall Harbor are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Betterton Beach and Gunpowder Falls State Park. 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
  • Washington College - 8 min walk
  • River Arts Chestertown - 11 min walk
  • Wilmer Park - 11 min walk
  • Rolphs Wharf Marina - 10 min drive

Getting around

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

Restaurants

  • McDonald's - 3 min drive
  • Procolino Pizza - 3 min drive
  • Dining Hall - 17 min walk
  • Luisas Cafe - 3 min drive
  • Uncle Charlie's Bistro - 2 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 0.4 mi (0.6 km) from Washington College and 4.7 mi (7.6 km) from Rolphs Wharf Marina. Betterton Beach and Rock Hall Harbor are also within 16 miles (25 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 17 out of 19 reviews" "
Rating 8 - Good. 2 out of 19 reviews" "
Rating 6 - Okay. 0 out of 19 reviews" "
Rating 4 - Poor. 0 out of 19 reviews" "
Rating 2 - Terrible. 0 out of 19 reviews" "

9.6/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

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

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

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

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

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

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
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