House in Maryland
10 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
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.
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.
Amenities
Non-smoking
No pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Jun 2026
We absolutely loved this property! The view when you first walk in is stunning and really sets the tone for the whole stay. The pool was a godsend, especially with the unseasonably hot 90-degree weather we had in early June.The town was charming, with some great little shops and restaurants to explore. We loved that every bedroom had its own bathroom, and the Sleep Number bed in the first-floor primary bedroom was such a nice surprise and very comfortable.The gas firepit on the dock was so relaxing! And the dock was lighted which we great for evening catfishing.The home had everything we needed, and the convenience of having a grocery store only about 12 minutes away was a huge plus. We had a wonderful stay and can’t wait to come back!
10 / 10Outstanding·Apr 2026
We we're in town for an Alumni weekend and had the best stay here! Everything was perfect, we have MORE than enough space, and had a great time with all the games in the house - such a fun bonus. We're already planning our next stay here!
10 / 10Outstanding·Dec 2025
It was a magical Christmas Holiday at the Christmas Cottage on the Chester River. We loved every moment from sunrise to sunset. We never left the house but had family come join us for breakfast, dinner, gift exchanging and relaxing by the water. We can’t wait for next year already.
10 / 10Outstanding·Aug 2025
A wonderfully relaxing stay!This property is impeccably maintained both indoors and outdoors. The kitchen is thoughtfully stocked with essentials, and the bedrooms and bathrooms are modern, spotless, and feature beautiful views of the lake.The pool is deep and inviting, with ample lounge seating for relaxation (note: the slide pictured is not available for use due to insurance restrictions). The setting is serene, with hummingbirds visiting the garden and sailboats gliding across the lake—an ideal spot for a peaceful retreat.
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Top rated by guests
10Outstanding
(44 Ratings)
"We absolutely loved this property! The view when you first walk in is stunning and really sets the tone for the whole stay. The pool was a godsend, especially with the unseasonably hot 90-degree weath..."
Stacey K.Don't miss out! Price and availability may change
