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.
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Chestertown
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
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
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
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 Crumpton Auction. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cave exploring and hiking.
Historical Society of Kent County Maryland - 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
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 7 May, 2026, prices found for a 1-night stay for 2 adults at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town on 12 May, 2026 start from S$919, 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.
Everything we needed was there. Owners next sore are super nice and hrphful.
steven s.
Stayed 3 nights in Jul 2025
Verified
10/10 Excellent
Mark
19 Sept, 2022
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.
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!
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.
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.
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.
Lauriann S.
Stayed 2 nights in Jul 2025
Response from VrboOwner on 18 Jul, 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.
Archival
10/10 Excellent
Laura D.
13 Oct, 2014
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.
Laura D.
Response from VrboOwner on 24 Mar, 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.
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!
Verified traveller
Stayed 2 nights in Jul 2021
Response from VrboOwner on 9 Aug, 2021
I am so glad you enjoyed your stay. We hope that you will come and visit again.
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!
Michael B.
Stayed 3 nights in May 2021
Response from VrboOwner on 17 Jun, 2021
I am so happy you enjoyed your stay and I hope to see you again in the future.
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!
Amber U.
Stayed 2 nights in Oct 2023
Response from VrboOwner on 13 Oct, 2023
Thank you for being the perfect guests. We look forward to your visits in the future.
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.
Elamurugan S.
Stayed 3 nights in Aug 2023
Response from VrboOwner on 20 Aug, 2023
We are very happy you enjoyed your stay at Chester River Dreams and look forward to your next visit.
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!
Morgan G.
Response from VrboOwner on 24 Mar, 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.
14 Sept, 2016
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.
Tim N.
Stayed 3 nights in Sep 2016
Response from VrboOwner on 24 Mar, 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.
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.
Patricia C.
Stayed 2 nights in Aug 2019
Response from VrboOwner on 24 Mar, 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
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.
James S.
Stayed 2 nights in May 2022
Response from VrboOwner on 30 May, 2022
The weather was very unfortunate. Please come back again and we will try harder for nice weather!😀
Archival
10/10 Excellent
morgan s.
30 Aug, 2014
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.
morgan s.
Response from VrboOwner on 24 Mar, 2020
We are thrilled that you enjoyed yourselves and hope to see you again.
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.
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