Entire home
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Riverside holiday home with kitchen and balcony
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, Washington College8 min drive
- Place, Historical Society of Kent County Maryland8 min drive
- Place, River Arts Chestertown9 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)66 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 Single 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
Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and 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. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and 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. This whole area is loaded with festivals. Here's a few more.
Bettertown days @ Betterton Beach usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.
FYI, the school zone has camera 24/7, so watch your speed.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and 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. This whole area is loaded with festivals. Here's a few more.
Bettertown days @ Betterton Beach usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.
FYI, the school zone has camera 24/7, so watch your speed.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Breakfast included
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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- Kitchen
- Washer
- Dryer
- Pet-friendly
9.8 out of 10, (94 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 23 kg 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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking. 
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
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 that there is a smoke detector on the property 
Safety features at this property include a fire extinguisher and a deadlock 
We should mention
A car is required for transport to and from this property
About the area
Chestertown
Located in Chestertown, this holiday home is on the waterfront. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Rolling Road Park and Chestertown Historic District. Travelling with kids? Consider Crumpton Auction and Hazel Miner Monument. Make sure you get close to the area's animals with activities such as game walks and birdwatching. 

Chestertown, MD
What's nearby
- Chestertown Dog Park - 6 min drive - 4.2 km
- Washington College - 8 min drive - 6.3 km
- Historical Society of Kent County Maryland - 8 min drive - 7.0 km
- River Arts Chestertown - 9 min drive - 7.3 km
- Rolphs Wharf Marina - 20 min drive - 16.0 km
Getting around
Restaurants
- Royal Farms - 7 min drive
- McDonald's - 7 min drive
- Royal Farms - 10 min drive
- Dunkin - 6 min drive
- Procolino's - 6 min drive
Frequently asked questions
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
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