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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Photo gallery for Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

A lakeside patio with outdoor seating and a view of the lake.
A residential house with a front porch, a lawn, and a driveway.
An indoor basketball court with multiple hoops, a polished floor, and a high ceiling with visible structural beams.
A spacious living area with a kitchen, dining table, and a large window providing natural light.
A living room with a stone wall, a fireplace, a television, a bookshelf, and a sofa.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Paddleboard available
    A rare find — hit the water on a paddleboard right here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Chestertown Historic District
4 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Chestertown, MD
  • Place, Kings Town Park
    ‪3 min walk‬
  • Place, Chestertown Historic District
    ‪19 min walk‬
  • Place, Washington College
    ‪4 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪55 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds and 1 Crib

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

About this property

Waterfront w/Deepwater Pier Walking Distance to Downtown 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.

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House Rules

Check in after 4:00 PM
Check out before 12:00 PM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Deposit will be forfeited if there is a gathering or event without permission. No guests of guests are allowed unless approved by owner.
No parties. No gatherings over the 8 guests who are listed in the rental request. No pets!
No pets.

Important information

You need to know

Property # 4487352
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 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
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

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the waterfront. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center are also worth visiting.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Kings Town Park - 3 min walk - 0.3 km
  • Chestertown Historic District - 19 min walk - 1.6 km
  • Garfield Center for the Arts at the Prince Theater - 4 min drive - 0.6 km
  • Historical Society of Kent County Maryland - 4 min drive - 0.6 km
  • Washington College - 4 min drive - 1.3 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪Milano's Pizzeria - ‬3 min drive
  • ‪McDonald's - ‬4 min drive
  • ‪Dunkin - ‬4 min drive
  • ‪Royal Farms - ‬3 min drive
  • ‪Procolino's - ‬4 min drive

Frequently asked questions

Is Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

As of 20 Aug, 2026, prices found for a 1-night stay for 2 adults at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown on 13 Nov, 2026 start from S$1,680, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

On-site parking is available at the property.

What time is check-in at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

Checkout is at 12:00 PM.

Where is Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown located?

Located in the heart of Chestertown, this holiday home is within 1 mile (2 km) of Kings Town Park, Historical Society of Kent County Maryland and Chestertown Historic District. Garfield Center for the Arts at the Prince Theater and Sumner Hall are also within 1 mile (2 km).

About the host

Hosted by Beth Connor

Host profile image
My husband and I live in Ellicott City and have wanted to buy a home on the water. We found a wonderful opportunity to purchase a great home to gather with our adult children, in a charming part of the world, that is not too far from our main residence. We hope that you too can enjoy our dream home with your family (and friends).

Why they chose this property

This home has a mix of antiques, and comfortable new, stylish furniture that today's vacationers want. The home was renovated with the most impeccable taste (we were fortunate to buy it this way). It has just about everything you would need to enjoy time together with your family and friends. From the huge screened porch with amazing new, chic outdoor furnishings (including an 8 foot farm table for crab picking or fancy dining), to a patio, hammock, canoe, paddle boards, fishing rods, crabbing net and trap, along with 4 adult bikes, this home will prove to be one of your family's more memorable experiences together. October through the end of April you can enjoy the use of the hot tub and fire pit. If you want to just relax indoors there is a large screened tv with a big sectional and chair to gather together. In the colder months, you can also enjoy the wood-burning fireplace (next to tv).

What makes this property unique

Walking/biking distance to Chestertown. Waterfront with pier. Gorgeously updated home with smart furnishings.

Languages:

English
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