Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Chestertown, Maryland
$527 avg/night
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end throughout the year. The home is also located just a short bike ride to Historic Chestertown, or you can even take one of our kayaks in while you enjoy the Chester River's rich wildlife.

Guests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings.

The three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun.

Minutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!

Chestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food.

About 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River.

With so many things to enjoy, book your experience today!

**Sheets are provided and beds made, but please bring towels**

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers On The Beach
  • DINING

    Dining Table
  • SAFETY

    No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Firepit Garden Outdoor Furniture Porch Or Lanai
  • POOL/SPA

    Sauna
  • BATHROOMS

    2 Bathrooms Hair Dryer Shower Soap Toilet Paper
  • WORKSPACES

    Desk
  • LANGS SPOKEN

    English Norwegian Spanish
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Cycling Nearby Ecotours Nearby Fitness Facilities Nearby Hiking Nearby Hiking/biking Trails Nearby Hunting Nearby Kayak On Site Power Boating Nearby Swimming Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books Foosball Table Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Games Playground Travel Crib
  • LOCATION HIGHLIGHTS

    In A Rural Location In A Village In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • 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 Wheelchair Accessible

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Rates & Availability

Review Review

  • Cory F.

    Submitted Jan 11, 2026

    Stayed Jan 8, 2026

    Location. Host was commutative and helped with process.

  • Michael F.

    Submitted Jan 2, 2026

    Stayed Dec 29, 2025

    Even in the darkest days around the winter solstice the beauty of the river at the house is a wonder. We welcomed in a new year by sweating out the old year in the sauna and by communing with the cacophonous geese and the stoic eagles. Wishing all of us new beginnings in 2026!

  • Nick O.

    Submitted Dec 11, 2025

    Stayed Dec 5, 2025

    Had a wonderful visit! Beautiful home

  • Michael F.

    Submitted Oct 27, 2025

    Stayed Oct 23, 2025

    We love spending quiet time on the idyllic Chester river. The house is a wonderful getaway.

  • Suzan B.

    Submitted Sep 30, 2025

    Stayed Sep 25, 2025

    This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.

  • Betsy W.

    Submitted Sep 25, 2025

    Stayed Sep 12, 2025

    Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.

  • victoria g.

    Submitted Jul 10, 2025

    Stayed Jun 27, 2025

    One of our favorite spots! Never disappoints.

  • John P.

    Submitted Jun 17, 2025

    Stayed Jun 2, 2025

    We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.

  • Amy K.

    Submitted Jun 9, 2025

    Stayed Jun 6, 2025

    This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.

  • Andrew M.

    Submitted May 25, 2025

    Stayed May 23, 2025

    Great house with an even greater view.

  • Carter F.

    Submitted Jan 12, 2025

    Stayed Jan 9, 2025

    Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.

  • Michael F.

    Submitted Oct 27, 2024

    Stayed Oct 24, 2024

    We have enjoyed our stays here in all seasons, but autumn is particularly beautiful with the leaves changing color and the migratory birds passing through. Such a great breather from city life.

  • Linda E.

    Submitted Oct 7, 2024

    Stayed Oct 3, 2024

    This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.

  • Jason S.

    Submitted Sep 30, 2024

    Stayed Sep 27, 2024

    Very beautiful views and relaxing. Our dog loved it too.

  • Karin C.

    Submitted Sep 23, 2024

    Stayed Sep 17, 2024

    It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.

  • Submitted Sep 22, 2024

    Stayed Sep 20, 2024

    Only two days but it was scenic and relaxing on the water.

  • Pat O.

    Submitted Jun 30, 2024

    Stayed Jun 22, 2024

    This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.

  • Cindy D.

    Submitted Jun 3, 2024

    Stayed May 17, 2024

    We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!

  • Suzan B.

    Submitted May 25, 2024

    Stayed May 10, 2024

    This was the perfect place to gather our family of 5 adults and our 3 fur babies to celebrate Mother’s Day over the weekend. The house is beautifully decorated and we thoroughly enjoyed the large property that was very private and had not only access to the water but also stunning views. We look forward to coming back.

Your dates are Available!

Total

Includes taxes and fees
$527+
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