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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
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Reviews
9.8 out of 10
Exceptional
6 bedrooms5+ bathroomsSleeps 14
Popular amenities
Explore the area

Chestertown, MD
- Place, Historical Society of Kent County Maryland6 min walk
- Place, Washington College8 min walk
- Place, River Arts Chestertown8 min walk
- Airport, Baltimore, MD (MTN-Martin State)106 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
Add dates for prices
Amenities
Kitchen
Washing machine
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
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
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 Larrabee Arts Center and Crumpton Auction. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Chestertown, MD
What's nearby
- Historical Society of Kent County Maryland - 6 min walk - 0.6 km
- Chestertown Historic District - 8 min walk - 0.7 km
- Washington College - 8 min walk - 0.7 km
- Garfield Center for the Arts at the Prince Theater - 8 min walk - 0.7 km
- River Arts Chestertown - 8 min walk - 0.7 km
Getting around
Restaurants
- Milano's Pizzeria - 4 min drive
- Royal Farms - 3 min drive
- Dunkin - 3 min drive
- McDonald's - 3 min drive
- Royal Farms - 5 min walk
Frequently asked questions
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 window9.6/10
Cleanliness
10/10
Check-in
9.4/10
Communication
9.8/10
Location
9.8/10
Listing accuracy
Reviews
Verified
6 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 5 nights in Oct 2025
Verified
8/10 Good
Harold L.
6 Aug 2024
Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication
Family Vacation
Harold L.
Stayed 5 nights in Aug 2024
Verified
10/10 Excellent
sandra l.
27 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House
sandra l.
Stayed 4 nights in Jul 2023
Verified
10/10 Excellent
David K.
23 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome stay on the Chester River
David K.
Stayed 5 nights in Sep 2024
Verified
10/10 Excellent
Helen C.
27 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family reunion
Helen C.
Stayed 21 nights in Jul 2023
Verified
10/10 Excellent
Thomas H.
20 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Looking for the perfect getaway? This is it!
Thomas H.
Stayed 7 nights in Jul 2024
Verified
8/10 Good
Janise F.
24 Aug 2023
Liked: Check-in, location, listing accuracy
Disliked: Communication
Bridgeway Community Church
Janise F.
Stayed 6 nights in Aug 2023
Verified
10/10 Excellent
Maggie E.
17 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay on the water for family and friends!
Maggie E.
Stayed 4 nights in May 2023
Verified
10/10 Excellent
Tony P.
31 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent House!
Tony P.
Stayed 6 nights in Aug 2022
Verified
10/10 Excellent
Michael K.
6 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for a relaxing family and friends get-together
Michael K.
Stayed 4 nights in Jul 2022
Verified
10/10 Excellent
Marilyn O.
18 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Relax at River in Chestertown
Marilyn O.
Stayed 7 nights in Jul 2022
Verified
10/10 Excellent
Kate s.
14 June 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place for a family gathering!
Kate s.
Stayed 4 nights in Jun 2022
Verified
8/10 Good
Ivonne R.
17 Oct 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Wedding Weekend
Ivonne R.
Stayed 3 nights in Oct 2021
Verified
10/10 Excellent
Wayne C.
27 Sept 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Weekend
Wayne C.
Stayed 3 nights in Sep 2021
Verified
10/10 Excellent
Tara R.
7 Sept 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Stay in Chestertown
Tara R.
Stayed 2 nights in Sep 2021
Verified
10/10 Excellent
Diane R.
21 Aug 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house and property
Diane R.
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Loren G.
24 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Fun
Loren G.
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
john s.
20 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown
john s.
Stayed 6 nights in Jul 2021
Verified
10/10 Excellent
Lori J.
12 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown's Best
Lori J.
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
Sara S.
25 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
It was great, we had family members from age 3 to 83 and everyone enjoyed themselves.
Sara S.
Stayed 5 nights in Jun 2021
Verified
10/10 Excellent
Alyson O.
15 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Home
Alyson O.
Stayed 4 nights in Jun 2021
Verified
10/10 Excellent
Keith P.
7 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great long weekend stay!
Keith P.
Stayed 3 nights in Jun 2021
Verified
10/10 Excellent
Bethany C.
8 Feb 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, incredible home
Bethany C.
About the host
Hosted by Diane Oliver
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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