Breathtaking waterfront home on the Chester River | House in Chestertown

10.0 (37 Reviews) |   4 Bedrooms  4 Bathrooms  10 Guests
Chestertown House | Breathtaking waterfront home on the Chester River

4 Bedroom House in Chestertown

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.

Breathtaking waterfront home on the Chester River is located in Chestertown. Breathtaking waterfront home on the Chester River provides accommodation, featuring Air Conditioner, Balcony/Terrace, Security/Safety, among other amenities. This House features Air Conditioner, Balcony/Terrace, Security/Safety, to make your stay a comfortable one.

Breathtaking waterfront home on the Chester River has 4 Bedrooms , 4 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
Pool
TV
Private Pool
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Fireplace/Heating
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Bathtub or shower
  • 4+ bathrooms
  • Towels provided
  • Toilet paper
Bedroom
  • Bed sheets provided
  • 4 bedrooms
  • Dining table
Kitchen
  • Cookware/dishes/utensils
  • Coffee/tea maker
  • Oven
  • Refrigerator
  • Kitchen island
  • Dishwasher
  • Microwave
  • Stovetop
Laundry
  • Washing machine and dryer
  • Laundry facilities
Parking
  • Onsite parking
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
Activities
  • Hiking nearby
  • Hiking/biking trails nearby
  • Water tubing nearby
  • Fitness facilities nearby
  • Jet skiing nearby
  • Golf nearby
  • Fishing nearby
  • Kayak on site
  • Swimming nearby
  • Hunting nearby
  • Ecotours nearby
Entertainment
  • Arcade/game room
  • Smart TV
General
  • English
  • Near a hospital
  • On the river
  • On the waterfront
Guest Services
  • Playground
  • Iron/ironing board
Internet
  • Free WiFi
Outdoors
  • Fenced yard
  • Firepit
  • Patio
  • Barbecue grill
Security/Safety
  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
Spa
  • Outdoor pool
  • Private pool

Policies

Check-in
Check-in time starts at 3:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
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 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 long-term renters welcome 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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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

Claire F.
Jun 26, 2025 09:33:52 PM
Review Score:   10
Summary: Our group of two families with kids had a fantastic time staying at this beautiful home. The pool was wonderful, the views were incredible, and everyone had fun on the river, thanks to the paddle boards and kayaks provided (including kids’ kayaks!). We would happily stay here again.
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