Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Top rated by guests
View from deck of brick patio, fire pit area, & pier w/ separate floating dock.
Water view from open kitchen.
New hot tub on deck - use in autumn and winter mostly. Propane grill new in 2024
Welcome to our home.
2nd Master Bedroom with water view and entrance to deck.
review stars
10Outstanding
(111 Ratings)
Guests loved the well-furnished house with outdoor seating, a huge screened-in porch by the river, spacious bedrooms, and a well-stocked kitchen. The host, Beth, was responsive and accommodating. Highly recommended for a relaxing vacation!
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
10 / 10
Outstanding(111 Ratings)

House in Chestertown, MD

8 guests · 4 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

Amenities at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

Non-smoking
No pets allowed
Family friendly

Map of Chestertown, MD


Ratings and reviews

10 / 10
Outstanding(111 Ratings)
review starsSummary of reviews
Guests loved the well-furnished house with outdoor seating, a huge screened-in porch by the river, spacious bedrooms, and a well-stocked kitchen. The host, Beth, was responsive and accommodating. Highly recommended for a relaxing vacation!
From real guest reviews summarized by AI
10 / 10Outstanding·Nov 2025
Beautiful home on the river! Kitchen fully stocked, all bedrooms and livings space very comfortable. Porch and fire pit enjoyed by all. Would definitely recommend and stay again.
10 / 10Outstanding·Nov 2025
This rental was an ideal choice for our visit to Chestertown. Communication with the hosts was consistently clear, readily available, and very transparent, making the entire process smooth and stress-free. The house is beautifully situated on the Chester River, offering spectacular views and frequent sightings of birds, whose lively antics on and around the river provided endless entertainment. The river is ever changing in its offerings to the occupants. Exploring the surrounding area was easy and enjoyable. The bakeries located in and around High Street, downtown, were just a one mile walk away, which took us over the Chester River Bridge and through the charming, historic colonial streets The rental featured excellent outdoor appointments. Although we did not use the hot spa, canoe, paddleboard, fishing rods, or croquet set, we thoroughly enjoyed relaxing around the fire pit in Adirondack chairs and taking the tandem kayak out on the river. The Chester River proved perfect for kayaking, and the screened porch at the back of the house provided a peaceful spot for relaxation and quiet enjoyment. Access by vehicle and parking were exceptionally easy and convenient. The house was very comfortable with 3 bedrooms perfect for couples and a nice 4th with twin beds. The 3 bathrooms were roomy and well lit. The kitchen was perfect for using goodies from the farmer’s market. We left feeling our visit with family was well celebrated & when not touring, relaxed. We would return!
10 / 10Outstanding·Oct 2025
This property was perfect for our stay; the home is beautiful and had all the space and amenities were exactly what we needed. The home was clean and very cozy, we felt at home for the event we were attending, we could not have asked for more. If you are attending a wedding at the
10 / 10Outstanding·Sep 2025
In town for wedding and stayed three nights. Pictures really don’t show the real beauty of this home. Quiet location, beautiful water views, well stocked and clean. Plenty of room for everyone. The host was very accommodating! Would definitely stay again.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.