Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown, Maryland
$515 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

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 thelarge 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.

Read More Expand
  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly
  • BEACH

    Beach Towels Near The Beach
  • DINING

    Dining Table Free Breakfast Available
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Recycling Unit Size: 2100 Sq Ft (195 Sq M) Uses Some LED Lighting Water-efficient Showers Only
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Dock Firepit Outdoor Furniture Patio
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Jet Skiing Nearby Kayak On Site Marina Nearby Sailing Nearby Water Skiing Nearby Water Sports Equipment Water Tubing Nearby Winery Tours Nearby
  • ENTERTAINMENT

    DVD Player Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Ceiling Fan Heating
  • FAMILY FRIENDLY

    Children's Dinnerware Children's Games Highchair
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Wet Bar
  • SUITABILITY/ACCESSIBILITY

    If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Tile Flooring In Public Areas

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Rates & Availability

Review Review

  • Mark

    Submitted Sep 19, 2022

    Stayed Sep 16, 2022

    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.

  • Josh M.

    Submitted Oct 27, 2025

    Stayed Oct 24, 2025

    Friendly owners and neighbors on a very quiet private road with unbeatable river views and access. The fishing right off the dock is great.

  • Kelly G.

    Submitted Sep 1, 2025

    Stayed Aug 29, 2025

    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!

  • steven s.

    Submitted Jul 25, 2025

    Stayed Jul 18, 2025

    Everything we needed was there. Owners next sore are super nice and hrphful.

  • Lauriann S.

    Submitted Jul 17, 2025

    Stayed Jul 11, 2025

    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.

  • Stephen H.

    Submitted Jun 7, 2025

    Stayed May 16, 2025

    We had a wonderful weekend. Thank you!

  • Sun P.

    Submitted Nov 8, 2024

    Stayed Nov 2, 2024

    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.

  • Sarah R.

    Submitted Jun 23, 2024

    Stayed Jun 21, 2024

    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.

  • Bob R.

    Submitted Jun 19, 2024

    Stayed Jun 14, 2024

    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!

  • Amber U.

    Submitted Oct 9, 2023

    Stayed Oct 6, 2023

    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!

  • Allie P.

    Submitted Sep 17, 2023

    Stayed Sep 15, 2023

    Home was very clean and neat. We enjoyed the snacks, and little touches.

Your dates are Available!

Total

Includes taxes and fees
$515+
View details