Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown | House in Chestertown

10.0 (103 Reviews) |   4 Bedrooms  3 Bathrooms  8 Guests
Chestertown House | Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

4 Bedroom House in Chestertown

My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boat & dock at our deep water pier. Crabbing* (trap & net), fishing (2 rods), & biking (4 provided) are also fun activities to enjoy here at the property. Fire pit (all seasons), indoor fireplace, and outdoor hot tub (available October through the end of April). We will do our best to keep hot tub in working order, but cannot guarantee it will be in working condition 100% of the time. It does take longer to get technicians out here. However we will do our best. We look forward to your stay. All are welcome.
*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown is located in Chestertown. Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown provides accommodation, featuring Air Conditioner, Entertainment, Internet, among other amenities. This House features Air Conditioner, Entertainment, Internet, to make your stay a comfortable one.

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown has 4 Bedrooms , 3 Bathrooms, and max occupancy of 8 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.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Amenities

Air Conditioner
Parking
TV
View
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Hot Tub
Internet
Kitchen
Laundry

Policies

Check-in
Check-in time starts at 4:00 pm minimum check-in age: 30
Check-out
Check-out before 12:00 pm
Child Policy
Children are welcome.
Pet Policy
Pets not allowed

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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip host has not indicated whether 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

Deborah P.
May 20, 2025 04:07:01 AM
Review Score:   10
Summary: We had a wonderful weekend stay with family for our daughter’s graduation from Washington College. The location was perfect, so convenient to town and campus. The house was lovely and immaculate. We highly recommend!
See All Reviews
Check House Availability
Nightly rates from:
USD $583
You will be redirected to  
Hot Deal - It has been viewed 230 times today
Not the right fit? Check out our other properties in Chestertown
Property Image From $291
         

Property Image From $168
         

|
7.8 (70 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Property Image From $501
         

Property Image From $182
         

9.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • View
Property Image From $199
         

|
9.6 (19 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $356
         

10.0 (70 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $1,758
         

|
New
House
  • Parking
  • Pet Friendly
  • Pool
Property Image From $191
         

10.0 (39 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $124
         

8.0 (232 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $457
         

Property Image From $499
         

5.0 (87 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Accessibility
Property Image From $254
         

Property Image From $334
         

Property Image From $298
         

9.8 (26 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Property Image From $159
         

9.6 (102 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool