You can look forward to free breakfast, a firepit, and laundry facilities at Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town. Adventurous travelers may like the kayaking at this vacation home. Stay connected with free in-room WiFi.
Reviews
9.89.8 out of 10
Exceptional
Entire home
3 bedrooms3 bathroomsSleeps 6195 sq m
Popular amenities
Breakfast included
Kitchen
Washer
Dryer
Pet friendly
Free WiFi
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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 amenities
Beach
Beach nearby
Beach towels
Internet
Available in the house: Free WiFi
Parking and transportation
Car required
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
Toaster
Dining
Free breakfast available
Dining table
Wet bar
Bedrooms
3 bedrooms
Bedsheets provided
Sofa bed
Bathroom
2.5 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Entertainment
DVD player
Games
Smart TV with cable/satellite channels
Video library
Outdoor areas
Barbecue grill
Dock
Firepit
Outdoor furniture
Patio
Laundry
Laundry facilities
Washer/dryer
Work spaces
Desk
Desk chair
Comfort
Air conditioning
Ceiling fan
Heating
Pets
Pet friendly
2 pets total (up to 50 lbs per pet)
Suitability/Accessibility
Tile flooring in public areas
Smoking not allowed
Services and conveniences
Iron/ironing board
Location highlights
Near a health/beauty spa
Near a hospital
Near an outlet shopping mall
Near the marina
On a river
On the waterfront
Things to do
Kayak
Water sports equipment
Basketball nearby
Birdwatching nearby
Cycling nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Hunting nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Sailing nearby
Spelunking nearby
Swimming nearby
Water skiing nearby
Water tubing nearby
Wildlife walks nearby
Winery tours nearby
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
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.
Pets
Pets allowed
Service animals are welcome, and are exempt from fees
2 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: 4 pets weighting over 60lbs, please contact owner.
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
We should mention
A car is required for transportation to and from this property
About the neighborhood
Located in Chestertown, this vacation 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. 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. Visit our Chestertown travel guide
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 50 lbs per pet. Some restrictions may apply, so please contact the property for more details.
How much is parking?
Onsite 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?
Check-out is at 10:00 AM.
Where is Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town located?
This family-friendly Chestertown vacation 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 mi (10 km).
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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!
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.
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!
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
Sep 19, 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.
Beautiful views of the river, tranquil neighborhood, great house. Perfect place to decompress and get away for a week.
John U.
Stayed 7 nights in Oct 2022
Archival
10/10 Excellent
Laura D.
Oct 13, 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.
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.
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!
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!
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.
Archival
8/10 Good
Tim N.
Sep 14, 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.
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.
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.