Entire home
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Family-friendly beachfront vacation home with free WiFi
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Reviews
1010 out of 10
Exceptional
Entire home
Popular amenities
- Dryer
- Beach view
- Washer
- Fireplace
Explore the area

Chestertown, MD
- Historical Society of Kent County MarylandPlace, Historical Society of Kent County Maryland5 min drive
- River Arts ChestertownPlace, River Arts Chestertown5 min drive
- Washington CollegePlace, Washington College5 min drive
- Easton, MD (ESN-Easton - Newnam)Airport, Easton, MD (ESN-Easton - Newnam)59 min drive
Room options
About the area
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
- Historical Society of Kent County Maryland - 5 min drive - 3.2 km
- River Arts Chestertown - 5 min drive - 3.5 km
- Washington College - 5 min drive - 3.8 km
- Chestertown Dog Park - 7 min drive - 5.2 km
- Rolphs Wharf Marina - 13 min drive - 8.3 km
Getting around
- Baltimore, MD (MTN-Martin State) - 106 min drive
Restaurants
- Milano's Pizzeria - 6 min drive
- Royal Farms - 5 min drive
- Royal Farms - 5 min drive
- Dunkin - 7 min drive
- Procolino's - 7 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**
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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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
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.
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