Entire home
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Photo gallery for Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town





Reviews
9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 62100 sq ft
Popular amenities
Explore the area

Chestertown, MD
- Place, Chestertown Dog Park5 min drive
- Place, Washington College5 min drive
- Place, Historical Society of Kent County Maryland7 min drive
- Airport, Baltimore, MD (MTN-Martin State)108 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Back bedroom
1 Queen Bed
Den
1 Double Sofa Bed
Front bedroom
1 Queen Bed
upstairs Bedroom
1 Queen Bed and 2 Twin Beds
2 bathrooms, 1 half bathroom
Central bath
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Powder room
Soap · Towels provided · Toilet
upstairs bathroom
Soap · Towels provided · Toilet · Shower only · Shampoo
Spaces
Deck or patio
Kitchen
Dining area
About this property
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
- Hot tub
- Kitchen
- Washer
- Dryer
10.0 out of 10, Exceptional, (107 reviews)
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
Events
No events allowed
Pets
Pets allowed: less than 50 lbs per pet (limit 2 pets total)
4 pets weighting over 60lbs, please contact owner.
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
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 indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
About the neighborhood
Chestertown
Located in Chestertown, this vacation home is on the waterfront. The area's natural beauty can be seen at Rolling Road Park and Chestertown Historic District, while Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights. Traveling with kids? Consider Larrabee Arts Center and Crumpton Auction. Be sure to check out the area's animals with activities such as game walks and birdwatching.

Chestertown, MD
What's nearby
- Chestertown Dog Park - 5 min drive - 4.2 km
- Washington College - 5 min drive - 4.9 km
- Historical Society of Kent County Maryland - 7 min drive - 7.0 km
- Garfield Center for the Arts at the Prince Theater - 7 min drive - 7.0 km
- Chestertown Historic District - 7 min drive - 7.0 km
Getting around
Restaurants
- Milano's Pizzeria - 10 min drive
- McDonald's - 7 min drive
- Dunkin - 6 min drive
- Royal Farms - 10 min drive
- Procolino's - 6 min drive
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Amenities
10/10
Property conditions & facilities
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
Oct 27, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Oct 2025
Verified
10/10 Excellent
steven s.
Jul 25, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
steven s.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
Mark
Sep 19, 2022
Liked: Cleanliness, amenities, property conditions & facilities, communication
Mark
Stayed 2 nights in Sep 2022
Verified
10/10 Excellent
Kelly G.
Sep 1, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Kelly G.
Stayed 3 nights in Aug 2025
Verified
10/10 Excellent
Stephen H.
Jun 7, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stephen H.
Stayed 3 nights in May 2025
Verified
10/10 Excellent
Karman S.
Jun 8, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house!
Karman S.
Stayed 7 nights in May 2022
Verified
10/10 Excellent
Bob R.
Jun 19, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location
Bob R.
Stayed 2 nights in Jun 2024
Verified
10/10 Excellent
Lisa V.
Aug 17, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend away
Lisa V.
Stayed 2 nights in Aug 2022
Verified
10/10 Excellent
Lauriann S.
Jul 17, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location for a Getaway
Lauriann S.
Stayed 2 nights in Jul 2025
Verified
10/10 Excellent
Sun P.
Nov 8, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location!
Sun P.
Stayed 3 nights in Nov 2024
Verified
10/10 Excellent
John U.
Nov 6, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Riparian Tranquility
John U.
Stayed 7 nights in Oct 2022
Verified
10/10 Excellent
Sarah R.
Jun 23, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect River Stay
Sarah R.
Stayed 2 nights in Jun 2024
Archival
10/10 Excellent
Laura D.
Oct 13, 2014
Girls weekend
Laura D.
Verified
10/10 Excellent
Allie P.
Sep 17, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home
Allie P.
Stayed 2 nights in Sep 2023
Verified
10/10 Excellent
Verified traveler
Jul 25, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location!
Verified traveler
Stayed 2 nights in Jul 2021
Verified
10/10 Excellent
Michael B.
Jun 1, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home on the water!
Michael B.
Stayed 3 nights in May 2021
Verified
10/10 Excellent
Amber U.
Oct 9, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family weekend at Washington College
Amber U.
Stayed 2 nights in Oct 2023
Verified
10/10 Excellent
Catherine M.
Sep 2, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay!
Catherine M.
Stayed 7 nights in Jul 2023
Verified
10/10 Excellent
Elamurugan S.
Aug 20, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown Vacation
Elamurugan S.
Stayed 3 nights in Aug 2023
Verified
10/10 Excellent
Elsie D.
Jun 24, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wedding weekend
Elsie D.
Stayed 2 nights in Jun 2022
Archival
10/10 Excellent
Morgan G.
Jul 18, 2014
Beautiful Views!!!
Morgan G.
Archival
8/10 Good
Tim N.
Sep 14, 2016
Great Cottage
Tim N.
Stayed 3 nights in Sep 2016
Verified
10/10 Excellent
Patricia C.
Aug 8, 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Waterfront fun
Patricia C.
Stayed 2 nights in Aug 2019
Verified
10/10 Excellent
James S.
May 11, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Too bad for the weather!
James S.
Stayed 2 nights in May 2022
Archival
10/10 Excellent
morgan s.
Aug 30, 2014
Family getaway
morgan s.
About the host
Hosted by Dianna or Russell
Russ & I discovered this area while boating over 25 years ago. We fell in love with Chestertown. We have always loved the country, but to be on the water too, only makes it that much better. We moved here full time a couple years ago & love every minute of it. Frankly, it was the best place to be sequestered during the pandemic. Chestertown enjoys many festivals during "normal" times & has a lot of history. There is always something to do of you want or just do nothing at all. Fishing & crabbing off the dock is one of our favorite happy hour pass times. We call it the "fishing hour." I enjoy birding & will be able to see that by the Osprey nest that was installed in '19 as well as being a purple martin landlord. Feel free to ask me all about them as I tend to their nest cavities during breeding season. I am also a potter & opened my own studio where you can purchase gifts or sign up for workshops & classes in both wheel & hand build techniques. The shop is located just 15 min. away in another small town (you'll notice that theme in these here parts) named Galena. In fact, those of you travelling from the north may very well pass it on your way here,
We just know that you will fall in love w/the area as much as we did & enjoy the tranquil setting.
We just know that you will fall in love w/the area as much as we did & enjoy the tranquil setting.
Why they chose this property
This property offers spectacular views of the Chester River from the Family room, Kitchen, Dining room, 1 of the 2 large bedrooms, Deck, & of course, from the fire pit dock. The family room features a queen sleeper sofa with air mattress & has the best view of the river. It also features: hardwood flooring, wet bar w/wine cooler, recessed lighting, ceiling fan, smart TV, & decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. Both bathrooms have been renovated. There is a full living room with a view of a large pond. Off street parking for up to 3 vehicles.
Located on a private a serene road that is great for walking or kids with bikes.
Located on a private a serene road that is great for walking or kids with bikes.
What makes this property unique
Chestertown, as well as many other small towns in the area, are rich in history. We are situated 40 min from Dover, 20 min from Rock Hall, 45 min to Annapolis, 35 min to premium outlets & Kent Narrows.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend(cancelled for 2021), Rock fish tournaments usually early June & mid Sept
Sunday, 4th of July weekend is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown & parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times.
Betterton days @ Betterton Beach usually the fist weekend in Aug
2nd weekend in Aug Rock Hall hosts pirate's weekend. Lots of people dress up. FUN!
Sultana down rigging late Oct/early Nov,
Early Oct is Rock Hall's Fall fest
Every Sat till noon in Chestertown's Fountain park, is the farmer's market
Lots of times, Fri or Sat eves(in season) they have entertainment in Fountain park
First Friday (all year,) a great time to explore the town. most stay open late & supply free snacks
Check the board as you enter town for fun filled activities.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend(cancelled for 2021), Rock fish tournaments usually early June & mid Sept
Sunday, 4th of July weekend is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown & parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times.
Betterton days @ Betterton Beach usually the fist weekend in Aug
2nd weekend in Aug Rock Hall hosts pirate's weekend. Lots of people dress up. FUN!
Sultana down rigging late Oct/early Nov,
Early Oct is Rock Hall's Fall fest
Every Sat till noon in Chestertown's Fountain park, is the farmer's market
Lots of times, Fri or Sat eves(in season) they have entertainment in Fountain park
First Friday (all year,) a great time to explore the town. most stay open late & supply free snacks
Check the board as you enter town for fun filled activities.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback
More Vacation Ideas
- Annapolis Vacation Rentals
- Baltimore Vacation Rentals
- Havre De Grace Vacation Rentals
- Betterton Vacation Rentals
- Centreville Vacation Rentals
- Easton Vacation Rentals
- Stevensville Vacation Rentals
- Rock Hall Vacation Rentals
- St. Michaels Vacation Rentals
- Worton Vacation Rentals
- Beach rentals in Chestertown
- Cabin rentals in Chestertown
- Condo rentals in Chestertown
- Cottage rentals in Chestertown
- Family rentals in Chestertown
- Family rentals in Stevensville
- Rentals with hot tubs in Chestertown
- Houseboat rentals in Annapolis
- House rentals in Chestertown
- House rentals in Easton
- House rentals in Elkton
- House rentals in Joppa
- Pet-Friendly rentals in Chestertown
- Pet-Friendly rentals in Easton
- Rentals with pool in Chestertown




























