At Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!, you can look forward to a firepit, a garden and a playground. For some rest and relaxation, visit the sauna. Stay connected with free in-room WiFi, with a speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as laundry facilities.
Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 10
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
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**
Property amenities
Beach
On the beach
Beach loungers
Pool/Spa
Sauna
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Ice maker
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
3 bedrooms
Bedsheets provided
Bathroom
2 bathrooms
Bathtub
Hair dryer
Shower
Soap
Toilet paper
Living spaces
Dining table
Fireplace
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.
In-room accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
In a rural location
In a village
In the city centre
Near a health/beauty spa
Near a hospital
Near an outlet shopping centre
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)
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 allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
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
On-site parties or group events are strictly prohibited
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
About the area
Located in Chestertown, this holiday home is in the city centre and on the beach. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Travelling with kids? Consider Crumpton Auction and The Mainstay. Kayaking and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and hunting nearby. Visit our Chestertown travel guide
Is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! pet-friendly?
Yes, this property allows dogs (limit 2 total).
How much is parking at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?
On-site parking is available at the property.
What time is check-in at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?
Check-in begins at 3:00 PM.
What time is check-out at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?
Checkout is at 11:00 AM.
Where is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! located?
Located in Chestertown, this beachfront holiday home is in the city centre and within 3 mi (5 km) of Kings Town Park, Roundtop Park and Chestertown Historic District. Wilmer Park and Rolling Road Park are also within 3 miles (5 km).
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.