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

10.0 (81 Reviews) |   Pet Friendly   3 Bedrooms  2 Bathrooms  10 Guests
Chestertown House | Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown!

3 Bedroom House in 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**

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! is located in Chestertown. Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! provides accommodation, featuring View, Security/Safety, Wellness Facilities, among other amenities. This House features View, Security/Safety, Wellness Facilities, to make your stay a comfortable one.

Private Waterfront Paradise w/Pier - Kayak to Historic Chestertown! has 3 Bedrooms , 2 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
TV
View
Ocean View
Balcony/Terrace
Accessibility
Security/Safety
Sports/Activities
Wellness Facilities
Spa
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Toilet paper
  • 2 bathrooms
  • Hair dryer
  • Soap
  • Shower
Bedroom
  • Bed sheets provided
  • 3 bedrooms
  • Dining table
  • Fireplace
  • Living room
Kitchen
  • Cookware/dishes/utensils
  • Ice maker
  • Coffee/tea maker
  • Oven
  • Refrigerator
  • Dishwasher
  • Microwave
  • Blender
  • Stovetop
Laundry
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • Beach sun loungers
  • On the beach
Parking
  • Onsite parking
Pet Friendly
  • Pet friendly
  • Welcoming dogs only
  • 2 total pets
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
Activities
  • Bicycle on site
  • Winery tours nearby
  • Hiking nearby
  • Hiking/biking trails nearby
  • Wildlife and game walks nearby
  • Fitness facilities nearby
  • Kayaking nearby
  • Power boating nearby
  • Cycling nearby
  • Kayak on site
  • Swimming nearby
  • Hunting nearby
Entertainment
  • Foosball table
  • Smart TV with cable/satellite service
  • Games
  • Books
General
  • English
  • Norwegian
  • Spanish
  • Near outlet shopping
  • Near a health or beauty spa
  • In a rural location
  • On the river
  • On the waterfront
  • Near a hospital
  • In the city center
  • In a village
  • Desk
Guest Services
  • Children's games
  • Travel crib
  • Children's books
  • Playground
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Garden
  • Outdoor furniture
  • Porch or lanai
  • Firepit
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector or gas appliances on the property)
Spa
  • Sauna

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
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
2 total pets note from host: please do not allow your pets on the furniture. pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy
Smoking is not permitted

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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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

Reviews

John P.
Jun 17, 2025 09:53:20 PM
Review Score:   10
Summary: 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.
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