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

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

Reviews

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washer and dryer
  • Air conditioning
  • Barbecue grill

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

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.
Our prices include all fees. No hidden fees.

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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. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cave exploring and hiking.
Map
Chestertown, MD

What's nearby

  • Washington College - 5 min drive - 4.9 km
  • Chestertown Dog Park - 5 min drive - 4.9 km
  • Rolling Road Park - 5 min drive - 4.9 km
  • Chestertown Historic District - 7 min drive - 7.0 km
  • River Arts Chestertown - 7 min drive - 7.3 km

Getting around

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

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

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 window
Rating 10 - Excellent. 78 out of 86 reviews
Rating 8 - Good. 7 out of 86 reviews
Rating 6 - Okay. 1 out of 86 reviews
Rating 4 - Poor. 0 out of 86 reviews
Rating 2 - Terrible. 0 out of 86 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

Verified

10/10 Excellent

Josh M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friendly owners and neighbors on a very quiet private road with unbeatable river views and access. The fishing right off the dock is great.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

steven s.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything we needed was there. Owners next sore are super nice and hrphful.
Stayed 3 nights in Jul 2025
Verified

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
Verified

10/10 Excellent

Kelly G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house and hospitality exceeded all expectations! We had a wonderful long weekend away and would definitely return. The kids especially loved fishing, kayaking, and the paddle boat. The farmer’s market was enjoyable Saturday morning, too. We had beautiful weather for yard games and the fire pit. Fantastic all around; highly recommend!
Stayed 3 nights in Aug 2025
Verified

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
Response from VrboOwner on Jun 8, 2022
You will be a welcome guest anytime!
Verified

10/10 Excellent

Stephen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful weekend. Thank you!
Stayed 3 nights in May 2025
Verified

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
Response from VrboOwner on Jun 19, 2024
Thank you for your review. We look forward to having you as guests again!
Verified

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
Verified

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
Verified

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
Response from VrboOwner on Nov 6, 2022
Thank you for being the perfect guests. We hope to see you again on your next trip back to the area!
Verified

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
Archival

10/10 Excellent

Laura D.

Girls weekend

Great, relaxing vacation. House is clean and beautiful with great backyard area. Owners are right next door and great hosts. Very quiet area with some good restaurants, a few bars, and a winery nearby.
Response from VrboOwner on Mar 24, 2020
I am so glad you enjoyed yourselves. We are hoping to do some more improvements to the property for next year. Hopefully you will get to come back again and see the results.
Verified

10/10 Excellent

Lauriann S.

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

Great Location for a Getaway

Perfectly situated for exploration of the area. You can explore the city of Chestertown or venture further afield to Annapolis. Perhaps you just want to rest and decompress? Take your coffee to the dock and watch the water. The house is charming and the kitchen is equipped for the best of meals. In a nutshell- this house is a gem! Definitely would recommend.
Stayed 2 nights in Jul 2025
Response from VrboOwner on Jul 18, 2025
Thank you for you wonderful review. You were the perfect guests. We look forward to hosting you on your next visit to the area.
Verified

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
Verified

10/10 Excellent

Verified traveler

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

Wonderful location!

My sister and I spent a weekend away at this property. It was very clean, extremely quiet, and the views incomparable. We spent the bulk of our time relaxing in the Adirondack chairs on the dock. With a constant breeze off the water, it was perfect!
Stayed 2 nights in Jul 2021
Response from VrboOwner on Aug 9, 2021
I am so glad you enjoyed your stay. We hope that you will come and visit again.
Verified

10/10 Excellent

Michael B.

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

Great home on the water!

This was a wonderful property right on the water with absolutely stunning views. The host was extremely responsive and a pleasure to interact with. I highly recommend this home to anyone looking for a relaxing stay on the water!
Stayed 3 nights in May 2021
Response from VrboOwner on Jun 17, 2021
I am so happy you enjoyed your stay and I hope to see you again in the future.
Verified

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
Response from VrboOwner on Oct 13, 2023
Thank you for being the perfect guests. We look forward to your visits in the future.
Verified

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
Response from VrboOwner on Sep 2, 2023
Thank you for being the perfect guests! We hope to see you again when you next visit the area.
Verified

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
Response from VrboOwner on Aug 20, 2023
We are very happy you enjoyed your stay at Chester River Dreams and look forward to your next visit.
Verified

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
Response from VrboOwner on Jun 24, 2022
We would love for you to come again
Archival

10/10 Excellent

Morgan G.

Beautiful Views!!!

This house was a perfect weekend getaway for my family and our children. We loved the house which has been newly renovated and the backyard was perfect to spend our days outside on the river! The house had everything we needed and Diana (the owner) was such a big help in making us feel comfortable. We would come back here in a heartbeat!
Response from VrboOwner on Mar 24, 2020
We enjoyed having you stay at the river house. It gives us great pleasure to know you enjoyed your time in Chestertown. We love it so much that we hope everyone who visits falls under it's spell as well. We would love for you to come back again.
Archival

8/10 Good

Tim N.

Great Cottage

We really enjoyed our stay. Worked really well for us. It is clean and roomy. The dock and the beach were great. My dog especially enjoyed the trip. He was in the water the whole time. Close to town. The owners were very nice as well.
Stayed 3 nights in Sep 2016
Response from VrboOwner on Mar 24, 2020
We are so happy that you enjoyed your visit. I am sorry that we were lacking in some way to prevent a 5 star rating. We strive to make your stay the best possible. We certainly hope to see you again in the future.Thank you for choosing to stay with us during your visit to the Chestertown area.
Verified

10/10 Excellent

Patricia C.

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

Waterfront fun

The location and the amenities were great. We had one issue that the owner quickly responded to. Really enjoyed the paddle boards, kayaks and the outside deck. The neighbors are friendly, the house is nice and has a beautiful view.
Stayed 2 nights in Aug 2019
Response from VrboOwner on Mar 24, 2020
Thank you for your review Patricia. We appreciate your generosity and forgiveness for the less than perfect accommodations. we of course would love to see you on the future if you are ever in the area again. All the best, Dianna
Verified

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
Response from VrboOwner on May 30, 2022
The weather was very unfortunate. Please come back again and we will try harder for nice weather!😀
Archival

10/10 Excellent

morgan s.

Family getaway

This was a perfect family getaway, super friendly neighbors, Dianna was wonderful and very helpful! The home was comfortable and very easy to be in for our 4 person family. Clean and very well decorated. Kiddo had a great time kayaking and crabbing off the dock. Brought the dog and he had a great time swimming and playing with the neighborhood friendly doggies too.
Response from VrboOwner on Mar 24, 2020
We are thrilled that you enjoyed yourselves and hope to see you again.
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