Entire home

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

Family-friendly beachfront vacation home with free WiFi

Choose dates to view prices

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

Property grounds
On the beach, sun loungers
Dining
Exterior detail
Smart TV, fireplace, foosball, books

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Chestertown, MD
  • Place, Kings Town Park
    ‪3 min drive‬
  • Place, Washington College
    ‪4 min drive‬
  • Place, Dover Downs Casino
    ‪56 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪130 min drive‬

Room options

About the neighborhood

Chestertown

On the beach.You'll find Kings Town Park and Roundtop Park within 2 miles (3 km) of this vacation home. Historical Society of Kent County Maryland and Chestertown Historic District are also within 3 miles (5 km).

What's nearby

  • Kings Town Park - 3 min drive - 1.1 miles
  • Chestertown Historic District - 4 min drive - 2.2 miles
  • Washington College - 4 min drive - 2.6 miles
  • Dover Downs Casino - 56 min drive - 42.0 miles
  • Dover International Speedway - 61 min drive - 42.0 miles

Getting around

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • ‪Milano's Pizzeria - ‬6 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Dunkin - ‬7 min drive
  • ‪Procolino's - ‬7 min drive
  • ‪Royal Farms - ‬5 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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**

Similar properties

Property amenities

Beach

  • On the beach
  • Beach loungers

Pool/Spa

  • Sauna

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Firepit
  • Garden
  • Outdoor furniture
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessibility
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • In the city center
  • 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

  • Bicycles
  • Foosball table
  • Kayak
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • No carbon monoxide detector or gas appliances (host has indicated there are no carbon monoxide detectors or gas appliances on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)

General

  • Bicycles
  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Service animals are exempt from fees
  • Note from host: Please do not allow your pets on the furniture.

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 indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a smoke detector in each accommodation.

Property is also known as

Vrbo Property

Frequently asked questions

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to the airport?

This vacation home is 73.2 mi (106-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to the beach?

This vacation home is on the beach. Don't forget your sunscreen!

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

No, there is no casino at this vacation home.

What time is check-in at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Check-in begins at 3:00 PM.

Is there free parking at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Free parking is not available at this vacation home.

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! have a pool?

This vacation home does not have a pool.

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! have a spa?

There are no spa services available at this vacation home.

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to downtown Chestertown?

This vacation home is 1.6 mi away from Chestertown.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 86 out of 91 reviews
Rating 8 - Good. 5 out of 91 reviews
Rating 6 - Okay. 0 out of 91 reviews
Rating 4 - Poor. 0 out of 91 reviews
Rating 2 - Terrible. 0 out of 91 reviews

9.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

David J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was great for families and pets. Very accessible waterfront for dogs. It had nice and relaxing fire pit area and outdoor sauna was a fun experience. The house had everything that we needed. Quick responses from host
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Nick O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wonderful visit! Beautiful home
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Betsy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Cory F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location. Host was commutative and helped with process.
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love spending quiet time on the idyllic Chester river. The house is a wonderful getaway.
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Shaun S.

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

Location was perfect

Loved our stay!
Stayed 3 nights in Oct 2021
Verified

10/10 Excellent

Hardeep S.

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

Great place and hours

Enjoyed our stay here
Stayed 2 nights in Jan 2022
Verified

10/10 Excellent

victoria g.

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

Weekend getaway

One of our favorite spots! Never disappoints.
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Andrew M.

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

Beautiful Location

Great house with an even greater view.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

David D.

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

Great family spot

Great place! Would love to stay in the summer when the weather is warmer and enjoy the outdoors. Enjoyed our time there with visiting with family.
Stayed 2 nights in Mar 2023
Verified

10/10 Excellent

Suzan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Carter F.

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

Weekend with friends

Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Sean & Jasmine R.

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

Excellent peaceful scenic stay

We enjoyed a peaceful getaway, with beautiful sunsets, and a cozy setting. Will definitely do again.
Stayed 3 nights in Aug 2021
Verified

10/10 Excellent

Doug B.

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

Great to work with owners

Wonderful in all aspects! Looking forward to our next stay!
Stayed 2 nights in Jul 2021
Verified

10/10 Excellent

Jason S.

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

Great

Very beautiful views and relaxing. Our dog loved it too.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Andrew E.

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

Great location and nice house

Lovely setup on the water
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Emily L.

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

Great place

A great place to relax and enjoy the Chester river and surrounding area. Rental has all the amenities. Can’t wait to go back!
Stayed 2 nights in Apr 2023
Verified

10/10 Excellent

Bryn M.

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

Weekend getaway

Beautiful home and property! Host was very communicative and even gave suggestions for places to go in town. Would definitely book again.
Stayed 2 nights in Apr 2024
Verified

10/10 Excellent

Debbie R.

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

Beautiful property on the water . House was well equipped -welcoming to guests , great place !!

Perfect experience
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Michael F.

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

Idyllic River Getaway

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.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Michael F.

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

Another relaxing stay at this bucolic riverfront getaway

We have been back to Ina's beautiful house several times and each time is a pleasure. We enjoy the quiet, the birds, the river's ebbs and flows, and the spectacular sunsets.
Stayed 3 nights in Apr 2023
Verified

10/10 Excellent

Kathryn W.

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

Great weekend!

Thank you for sharing your wonderful home with us! Everything was perfect for our stay-we look forward to staying again soon!
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Patricia D.

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

Chestertown rental

Great house, beautiful waterfront property!
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Lynda M.

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

Lovely Listing

The illuminated pier at night was a treat!
Stayed 4 nights in Feb 2023