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

looking down river from the dock
view from deck. Also fire pit to right.
view from dock.
front
looking up river from the dock

Reviews

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 62100 sq ft

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Breakfast included
  • Parking available
  • Kitchen

Explore the area

Map
Chestertown, MD
  • Washington College
    ‪7 min drive‬
  • Historical Society of Kent County Maryland
    ‪8 min drive‬
  • River Arts Chestertown
    ‪8 min drive‬
  • Aberdeen, MD (APG-Phillips Army Airfield)
    ‪92 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.

Property manager

Dianna or Russell
Premier Host

Languages

English
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Amenities

Breakfast included
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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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
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Events

No events allowed
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Pets

Pets allowed: less than 23 kg per pet (limit 2 pets total)
4 pets weighting over 60lbs, please contact owner.
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Smoking

Smoking is not permitted
Beach towels are not provided. Do not use bath towels for beach or pets. No wet pets in the house, No pets on the furniture. Do not use bedding 4 pets
Smoking is permitted outside the house. Take care not to let smoke inside. Extra fees may be charged if cigarette/cigar odors are inside the house.
Minimum of 2 night are required EXCEPT for holidays. Minimum of 3 nights for ALL holidays. NO SATURDAY check- in for 7 days or longer.

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. The area's natural beauty can be seen at Rolling Road Park and Wilmer Park, while Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights. 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.
Map
Chestertown, MD

What's nearby

  • Washington College - 7 min drive - 5.2 km
  • Garfield Center for the Arts at the Prince Theater - 8 min drive - 6.0 km
  • Historical Society of Kent County Maryland - 8 min drive - 6.0 km
  • River Arts Chestertown - 8 min drive - 6.1 km
  • Rolphs Wharf Marina - 17 min drive - 13.1 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 110 min drive

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Dining Hall - ‬7 min drive
  • ‪Procolino Pizza - ‬6 min drive
  • ‪China House - ‬6 min drive
  • ‪The Freeze - ‬6 min drive

Frequently asked questions

Is Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town?

Check-in begins at 4:00 PM.

What time is check-out at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town?

Checkout is at 10:00 AM.

Where is Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town located?

This family-friendly Chestertown holiday home is located on the waterfront, within 3 mi (5 km) of Chestertown Dog Park and Rolling Road Park. Wilmer Park and Kings Town Park are also within 6 miles (10 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. 72 out of 80 reviews
Rating 8 - Good. 7 out of 80 reviews
Rating 6 - Okay. 1 out of 80 reviews
Rating 4 - Poor. 0 out of 80 reviews
Rating 2 - Terrible. 0 out of 80 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Sun P.

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

Great location!

Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts.
Stayed 3 nights in Nov 2024

10/10 Excellent

Sarah R.

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

Perfect River Stay

House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay.
Stayed 2 nights in Jun 2024

10/10 Excellent

Bob R.

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

Great location

Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!
Stayed 2 nights in Jun 2024

10/10 Excellent

Amber U.

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

Family weekend at Washington College

We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!
Stayed 2 nights in Oct 2023

10/10 Excellent

Allie P.

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

Great home

Home was very clean and neat. We enjoyed the snacks, and little touches.
Stayed 2 nights in Sep 2023

10/10 Excellent

Catherine M.

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

Great stay!

Very nice owner. Super helpful and dealt with our leaving stuff! Mailed the oops we left that so nicely. Cheers!
Stayed 7 nights in Jul 2023

10/10 Excellent

Elamurugan S.

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

Chestertown Vacation

The property was awesome. We kayaked, kids enjoyed paddle boats, and relaxing by the water. The owners were excellent hosts. Chestertown farm market on saturday(s) is a must see. Dog friendly township. Will go back next summer.
Stayed 3 nights in Aug 2023

10/10 Excellent

Maureen H.

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

Lovely place!

We had a lovely stay at this cottage on the water. The cottage had its own dock, deck, mini beach, grassy yard with kayaks, paddle boat, stand up paddles —enough for everyone. The birding is brilliant. The hosts have created an environment that welcomes birds. On our morning paddle, we saw bald eagles, ample herons, other sea birds and an otter, snakes and turtles. The house has everything you need. It’s very comfortable with a full kitchen, games, plenty of different spaces to relax and enjoy your time with family. The hosts are super considerate and kind people. They know how to make a space that’s great for your holiday. Book now! You won’t regret it!
Stayed 2 nights in Jul 2023

10/10 Excellent

Bill F.

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

Eastern Shore Visit

My wife and I and our 3 grandchildren had an absolutely fabulous time on the Chester River. The cottage accommodated us very well with a modern kitchen and 2tv spaces The dock offered a fishing spot and beautiful views. Our hosts, Dianna and Russ made the experience special by making sure the kids knew how to use the kayaks and where to swim and generally helping them enjoy themselves. A short ride to Rockhall for crabs and a fishing trip topped off a wonderful Eastern Shore Visit.
Stayed 3 nights in Jul 2023

10/10 Excellent

Doris O.

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

Escape

I picked this property out based on the listing description. My family and guests were skeptical coming into the weekend about what I had picked out! Everyone, from start to finish had a blast! We kayaked, threw fishing lines in the water. We offered to take the family to dinner the first night and they asked for burgers on the grill! We made s’mores. Watched fireworks from the pier. Played board games, watched movies. Went to a festival nearby. Had a few meals out at local spots. There were many special touches that could be pointed out. I have already shared with my friends. I hope to get back again. Unplug, relax, enjoy! Heaven.
Stayed 4 nights in Jul 2023

10/10 Excellent

Ellen H.

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

Memorial weekend stay

Comfortable, well equipped rental home. Enjoyed all the amenities, with the dock and deck and lovely views of the river. Enjoyed sunrise one morning and watching the river come to life with the birds, and early morning scullers rowing. Had a cookout one night and lit a fire in the fire pit. So fun.
Stayed 3 nights in May 2023

10/10 Excellent

Cindy R.

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

Wonderful Chester River Property

Very clean, tidy home directly on the Chester river. While we were here for an event at Washington College in February, the property is gorgeous and we definitely want to return during warmer months to enjoy Chestertown and sipping wine on the deck overlooking the river. The house has lots of seating throughout and we enjoyed playing card games at night with the kids. Super clean house, and kitchen is incredibly functional. Can't wait to return!
Stayed 2 nights in Feb 2023

10/10 Excellent

John U.

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

Riparian Tranquility

Beautiful views of the river, tranquil neighborhood, great house. Perfect place to decompress and get away for a week.
Stayed 7 nights in Oct 2022

10/10 Excellent

Verified traveller

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

Wonderful well-equipped and comfortable house!

We visited Chestertown for a fall weekend of bird-watching and exploring. When we arrived, a bald eagle was perched right near the dock, so our birdwatching got off to a great start. We were delighted with the house- comfortable beds, immaculately clean, well-equipped with everything we needed, and lots of nice little touches to make our stay comfortable and enjoyable. One of our two nights was rainy and cold, so we stayed in and made dinner. We found everything we needed in the kitchen. We will definitely return and love that we were able to bring our dog. Thanks for a great stay!
Stayed 2 nights in Oct 2022

10/10 Excellent

Mark

Liked: Cleanliness, amenities, property conditions & facilities, communication
We had a wonderful stay. House was clean and charming, beds were comfy, hosts were attentive and nice, views were amazing. We enjoyed our visit very much.
Stayed 2 nights in Sep 2022

10/10 Excellent

Lisa V.

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

Weekend away

Excellent hosts. Everything we needed. Beautiful views!
Stayed 2 nights in Aug 2022

10/10 Excellent

Debbie L.

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

Stay

It was fun.
Stayed 3 nights in Aug 2022

10/10 Excellent

Karin C.

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

A lovely respite

We came for a few days to relax on the water. The view was wonderful, and we loved sitting on the dock watching the river. Diana was welcoming and informative, filling us in on the local bird life, from ducks to Great Horned Owls. A pair of ospreys were still guarding their nest just off the dock and we saw an eagle and a vulture. Unfortunately we were there during an intense heat wave which discouraged us from kayaking, but we look forward to it next time. The house is wonderfully complete with comfortable furniture and a well-equipped kitchen and is meticulously clean. We would have liked to stay longer and hope to return.
Stayed 3 nights in Aug 2022

10/10 Excellent

Jeff B.

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

Title

Great views!
Stayed 3 nights in Jun 2022

10/10 Excellent

Elsie D.

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

Wedding weekend

Very clean. Beautiful view.
Stayed 2 nights in Jun 2022

10/10 Excellent

Karman S.

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

Great house!

Great house, very clean, nice location, very attentive owners!
Stayed 7 nights in May 2022

10/10 Excellent

Glenn K.

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

Amazing Property

We had an amazing time staying on this property. We were visiting Washington college right by and it was a great location! Dianna was great and was responsive with everything asked, friendly neighbors as well! Would recommend this place for anyone
Stayed 2 nights in Apr 2022

10/10 Excellent

James S.

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

Too bad for the weather!

I certainly wish the weather cooperated as the backyard, the dock and Adirondack chairs were very inviting! The house was as described and made for a very homey weekend.
Stayed 2 nights in May 2022

10/10 Excellent

Lizeth M., Virginia

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

Great place

This house is amazing, comfy, great view
Stayed 2 nights in Oct 2021

10/10 Excellent

Sheldon J.

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

Very comfortable and relaxing.

Wonderful views of eagles and other birds. Enjoyed kayaking on River.
Stayed 7 nights in Sep 2021

About the host

Hosted by Dianna or Russell

Host profile image
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.

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.

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.

Languages:

English

Premier Host

They consistently provide great experiences for their guests