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

Kent County, Maryland 21620, United States
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Amenities
Hiking
Sauna
Basketball Court
Wi-Fi in Public Areas
No Smoking in Public Areas
Garden
Kayaking
Sailing
All amenities
Property Description
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**About pets:Pets allowed: dogs (limit 2 total).Please do not allow your pets on the furniture..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
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9.8/10
Outstanding
Cleanliness9.8
Amenities9.8
Location9.8
Service9.8
All 34 reviews
Surroundings
Airport: Easton Airport
(53.2km)
Train: Aberdeen Amtrak
(93.3km)
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Overview

Rooms

Guest Reviews

Services & Amenities

Policies

Host

7

3 Bedrooms Private Vacation Home

3 bedrooms: 1 bunk bed 2 single beds 2 queen beds and 1 king bed
Non-smoking
Room Details
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Guest Reviews

9.8/10
Outstanding
34 reviews
Verified Reviews
  • Cleanliness9.8
  • Amenities9.8
  • Location9.8
  • Service9.8
Average for similar properties in Kent County
Most Mentioned
A‍m‍y‍ ‍K‍.
June 10, 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.
v‍i‍c‍t‍o‍r‍i‍a‍ ‍g‍.
July 11, 2025
Weekend getaway One of our favorite spots! Never disappoints.
C‍a‍r‍t‍e‍r‍ ‍F‍.
January 12, 2025
Weekend with friends Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
A‍n‍d‍r‍e‍w‍ ‍M‍.
May 26, 2025
Beautiful Location Great house with an even greater view.
M‍i‍c‍h‍a‍e‍l‍ ‍F‍.
October 28, 2024
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.
P‍a‍t‍ ‍O‍.
July 1, 2024
Wonderful Vacation 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.
V‍e‍r‍i‍f‍i‍e‍d‍ ‍t‍r‍a‍v‍e‍l‍e‍r
September 23, 2024
Relaxing Only two days but it was scenic and relaxing on the water.
C‍i‍n‍d‍y‍ ‍D‍.
June 4, 2024
Wonderful Place on the River in Chestertown 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.
May 25, 2024
Relax, Recharge & Reconnect 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.

Services & Amenities

More Amenities
Internet
Public areas
Health & wellness
Activities
Cleaning services
Facilities for children
Accessibility

Property Policies

Check-in and Check-out Times
Check-in: after 15:00
Check-out: Before 11:00
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.

Cots and Extra Beds
Please contact the hotel for details about cot and extra bed policies.

Age Requirements
The main guest checking in must be at least 21 years old

Property host

Ina Herrera
Speaks: English, Spanish, Norwegian

About this property

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**About pets:Pets allowed: dogs (limit 2 total).Please do not allow your pets on the furniture..About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
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Frequently Asked Questions

What is the cancellation policy for Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

The cancellation policy for Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! varies depending on the type of room and booking conditions.

How much does it cost at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Prices at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! change according to dates, hotel policy, and other factors. Please search for the dates you wish to stay to view prices.

What are Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! nearby landmarks?

Nearby attractions to Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! include The Mill of Kingstown, only 1.7km from your search (straight-line distance) away.

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

Check-in at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! starts from 15:00, and the standard check-out time is by 11:00.

About This Property

Nearest AirportEaston
Distance to Airport53.15KM
Nearest Train StationAberdeen Amtrak
Distance to Train Station93.35KM
Hotel Star Rating4