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

A deck with a table and chairs, overlooking a lake with docks and a grassy area.
A bedroom with two beds, a white crib, a painting on the wall, a door, and a TV mounted on the wall.
A modern kitchen with granite countertops, stainless steel appliances, and wooden cabinetry.
A living room with a fireplace, a television, and a ceiling fan.
A living room with a grey sofa, a white coffee table, and a kitchen area with wooden cabinets and a countertop.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Overlooking the river
    Guests like the scenic riverfront location.

Popular amenities

  • Balcony or patio
  • Breakfast included
  • Barbecue
  • Pet-friendly
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Chestertown, MD
  • Place, Washington College
    ‪5 min drive‬
  • Place, Chestertown Dog Park
    ‪5 min drive‬
  • Place, Chestertown Historic District
    ‪7 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 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

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

View from deck of brick patio, fire pit area, & pier w/ separate floating dock.
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Chestertown
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (117 reviews)
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Rolling Road 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 Larrabee Arts Center and Schooner Sultana. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and hiking.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Washington College - 5 min drive - 4.9 km
  • Chestertown Dog Park - 5 min drive - 4.9 km
  • Chestertown Historic District - 7 min drive - 7.0 km
  • Historical Society of Kent County Maryland - 7 min drive - 7.0 km
  • River Arts Chestertown - 7 min drive - 7.0 km

Getting around

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

Restaurants

  • ‪Royal Farms - ‬10 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Dunkin - ‬6 min drive
  • ‪Procolino's - ‬6 min drive
  • ‪Royal Farms - ‬7 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. Some restrictions may apply, so please contact the property for more details.

How much does it cost to stay at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town?

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town on 25 April 2027 start from NZ$2,610, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town?

On-site parking is available at the property.

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. Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 81 out of 89 reviews
Rating 8 - Good. 7 out of 89 reviews
Rating 6 - Okay. 1 out of 89 reviews
Rating 4 - Poor. 0 out of 89 reviews
Rating 2 - Terrible. 0 out of 89 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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We very much enjoyed our stay. We were in town for a wedding. When we weren't involved in family activities, the house with the river front setting offered a tranquil retreat. I very much enjoyed just sitting in an Adirondack chair on the pier, while the younger folks got out on the paddle boards.
Stayed 3 nights in Oct 2026
Response from VrboOwner on 13 October 2026
Thank you for being the perfect guests. We hope to see you again during your next visit to the area!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very stress free experience
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and private setting on the river
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 8 June 2022
You will be a welcome guest anytime!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 19 June 2024
Thank you for your review. We look forward to having you as guests again!
Verified review

10/10 Excellent

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

Weekend away

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

10/10 Excellent

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 6 November 2022
Thank you for being the perfect guests. We hope to see you again on your next trip back to the area!
Verified review

10/10 Excellent

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

10/10 Excellent

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 24 March 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 review

10/10 Excellent

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
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 9 August 2021
I am so glad you enjoyed your stay. We hope that you will come and visit again.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 17 June 2021
I am so happy you enjoyed your stay and I hope to see you again in the future.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 13 October 2023
Thank you for being the perfect guests. We look forward to your visits in the future.
Verified review

10/10 Excellent

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 2 September 2023
Thank you for being the perfect guests! We hope to see you again when you next visit the area.
Verified review

10/10 Excellent

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

Wedding weekend

Very clean. Beautiful view.
Stayed 2 nights in Jun 2022
Response from VrboOwner on 24 June 2022
We would love for you to come again
Verified review

10/10 Excellent

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 20 August 2023
We are very happy you enjoyed your stay at Chester River Dreams and look forward to your next visit.
Archival

10/10 Excellent

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 24 March 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

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 24 March 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 review

10/10 Excellent

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 18 July 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.
Tell us how we can improve our siteShare feedback