Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
Highlights
Cook, dine, and unwind
Top-rated for its fully equipped kitchen, perfect for every meal.
Outdoor pool
The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
Centrally-located
You're never far from where you need to be with this convenient location.
Sleeps 10•4 bedrooms•9 beds
Popular amenities
Private pool
Onsite parking available
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Chestertown, MD
Chestertown Historic District
Place, Chestertown Historic District
2 min drive
Garfield Center for the Arts at the Prince Theater
Place, Garfield Center for the Arts at the Prince Theater
2 min drive
Washington College
Place, Washington College
2 min drive
Baltimore, MD (MTN-Martin State)
Airport, Baltimore, MD (MTN-Martin State)
127 min drive
Rooms & beds
4 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 King Bed and 2 Single Beds
Bedroom 4
2 Single Bunk Beds and 2 Single Beds
4 bathrooms, 1 half bathroom
1st Floor Master
Toilet · Shower only
2nd Floor Bunk Room
Bathtub or shower · Toilet
2nd Floor King Suite Bathroom
Toilet · Shower only
2nd Floor Quuen Suite
Toilet · Shower only
Downstairs Half Bath
Toilet
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
About this property
Breathtaking waterfront home on the Chester River
Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated entry past your private pool and extensive landscaping to a spectacular vista sweeping the riverfront. Bring your own boat or simply enjoy the recently updated custom Ipe deck featuring pier and floating dock for easy access to the water. Private beach with walk-in sandy river access is perfect for enjoying provided kayaks (1 adult and 2 child), stand-up paddleboards (2), life jackets included.
Enjoy your morning coffee from the expansive screened porch featuring 180-degree views of the beautiful Chester River. Amenities abound with a hot tub on the additional poolside deck, outdoor shower, provided pool floats, pool basketball and two adult bicycles (bring your own helmets).
The completely renovated and beautifully furnished home features a fully-equipped chef’s kitchen, bar seating and table for 8, sectional sofa and additional seating, bar height table, large screen TV, powder room and first floor master bedroom with magnificent en suite master bath and desk area.
Upstairs, there are three additional bedrooms (1 K, 1 Q) each with a private and updated full bath and access to a waterfront balcony that spans the home. The bunkroom features two sets of twin bunkbeds with trundles and includes gaming system, TV and comfortable kid-sized seating.
Take a short bike ride or walk into historic Chestertown to explore this quaint, historic town. Enjoy the farmer’s market every Saturday, speakeasy, cat café, whiskey distillery, River Packet boat cruise daily, wine and tapas bar, shops and multiple outstanding dining options. Check the town calendar and learn more at www.townofchestertown.com to schedule your visit to take advantage of the many special events held throughout the year. End your day gathered around the firepit to watch the blue herons and ospreys as the sun sets on another day in paradise.
Ask about discounted rates for extended stays.
Property information & notes: - Swimming pool & hot tub open May 1-Oct. 1. Slide is not available for rental use. - Ample parking for 3-4 vehicles - First floor gas fireplace - Gas Grill with provided propane - Outdoor firepit - Upstairs and downstairs full-size washer and dryer - Freshly-laundered sheets & bath and beach towels are provided for your use - Starter pack of shampoo, soap and toothpaste provided - WiFi throughout property - 4 TV’s with Apple TV and Firestick - NO SMOKING INSIDE OR OUTSIDE ON THE PROPERTY – will result in immediate eviction - NO PETS - Please exercise caution when opening and closing the wall of sliding pocket doors. See instructions in welcome packet. - Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. - Please respect the neighbors and neighborhood.
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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
Long-term renters welcome
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 on the waterfront. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Crumpton Auction and The Mainstay are also worth visiting. Discover the area's water adventures with jet skiing and waterskiing nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.
Chestertown Historic District - 2 min drive - 2.1 km
Garfield Center for the Arts at the Prince Theater - 2 min drive - 2.1 km
Washington College - 2 min drive - 2.8 km
Getting around
Baltimore, MD (MTN-Martin State) - 108 min drive
Restaurants
Milano's Pizzeria - 5 min drive
McDonald's - 5 min drive
Dunkin - 4 min drive
Royal Farms - 5 min drive
Cafe Sado - 3 min drive
Frequently asked questions
Does Breathtaking waterfront home on the Chester River have a pool?
Yes, this property has an outdoor pool.
How much does it cost to stay at Breathtaking waterfront home on the Chester River?
As of 20 Aug, 2026, prices found for a 1-night stay for 2 adults at Breathtaking waterfront home on the Chester River on 13 Nov, 2026 start from S$2,240, 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.
Is Breathtaking waterfront home on the Chester River pet-friendly?
No, pets are not allowed at this property.
How much is parking at Breathtaking waterfront home on the Chester River?
On-site parking is available at the property.
What time is check-in at Breathtaking waterfront home on the Chester River?
Check-in begins at 3:00 PM.
What time is check-out at Breathtaking waterfront home on the Chester River?
Checkout is at 10:00 AM.
Where is Breathtaking waterfront home on the Chester River located?
Situated on the waterfront, this holiday home is within 1 mile (2 km) of Wilmer Park, Sumner Hall and Chestertown Historic District. River Arts Chestertown and Garfield Center for the Arts at the Prince Theater are also within 1 mile (2 km).
About the host
Hosted by Peter Heller
Languages:
English
Premier Host
They consistently provide great experiences for their guests