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Breathtaking waterfront home on the Chester River

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Pool
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Property grounds
Lake
Property grounds

Reviews

10 out of 10

Exceptional

4 bedrooms4+ bathroomsSleeps 10

Popular amenities

  • Pool
    Pool
  • Parking available
    Parking available
  • Washer
    Washer
  • Outdoor space
    Outdoor space
  • Barbecue grill
    Barbecue grill
  • Kitchen
    Kitchen

Explore the area

Map
Chestertown, MD
  • Wilmer Park
    13 min walk
  • River Arts Chestertown
    18 min walk
  • Garfield Center for the Arts at the Prince Theater
    19 min walk
  • Aberdeen, MD (APG-Phillips Army Airfield)
    92 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
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.

Property manager

Peter Heller
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Free WiFi
Air conditioning

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Beautiful, spacious waterfront home, an easy walk to historic Chestertown
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Dryer
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9.8 out of 10, (22 reviews)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown

House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

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

About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. Rock Hall Harbor and Queenstown Harbor Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Betterton Beach and Eastern Neck National Wildlife Refuge. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Chestertown, MD

What's nearby

  • River Arts Chestertown - 18 min walk
  • Garfield Center for the Arts at the Prince Theater - 19 min walk
  • Historical Society of Kent County Maryland - 20 min walk
  • Washington College - 3 min drive
  • Rolphs Wharf Marina - 12 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 94 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Dining Hall - ‬4 min drive
  • ‪Procolino Pizza - ‬4 min drive
  • ‪China House - ‬4 min drive
  • ‪The Freeze - ‬4 min drive

Frequently asked questions

Does Breathtaking waterfront home on the Chester River have a pool?

Yes, this property has an outdoor pool.

Is Breathtaking waterfront home on the Chester River pet-friendly?

No, pets are not allowed at this 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 1.5 mi (2.4 km) from Washington College and within 16 miles (25 km) of Betterton Beach and Rock Hall Harbor. Eastern Neck National Wildlife Refuge and Queenstown Premium Outlets are also within 25 miles (40 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 25 out of 25 reviews" "
Rating 8 - Good. 0 out of 25 reviews" "
Rating 6 - Okay. 0 out of 25 reviews" "
Rating 4 - Poor. 0 out of 25 reviews" "
Rating 2 - Terrible. 0 out of 25 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

karin b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hidden treasure on the river
We had an incredible stay at the house. The views from every room in the house were stunning . Stayed with family ages 3 to 89 and everyone was comfortable. Kitchen was wonderful and had everything you would need to cook and in perfect shape.We enjoyed being able to bring our boat and tie up to the dock. Chestertown is a mile away and has much to offer with wonderful shops and restaurants. Can’t wait to go back.
Stayed 3 nights in Oct 2024

10/10 Excellent

Richard A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
A very comfortable, very clean and family-friendly place. The amenities were great. Area is quiet. Beautiful view of the sunrise.
Stayed 4 nights in Oct 2024

10/10 Excellent

Christine C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property!
Great house. Perfect location. Wonderful host.
Stayed 4 nights in Jul 2024

10/10 Excellent

Michelle W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Getaway
The house and property more than lived up to our expectations. We enjoyed floating the day away in the pool and kayaking in the morning. The kitchen had everything we needed to make dinner at night and the living room and screened in porch were comfortable to read and relax in the evening. Our family is already talking about coming back!
Stayed 7 nights in Jul 2024

10/10 Excellent

Kimberly D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing Beauty on the Chester River
We were delighted with this lovely home! Family of 9 had a super time (age range 4-62). Amazing water views from every space on the river side of the house. Peaceful and quiet, we enjoyed watching the different birds, the sunrises and the interesting boats and water activities especially from the large screened porch room. We also enjoyed paddle boarding and kayaking on the river and swimming in the wonderful pool! We loved the thoughtful design and layout of the downstairs common areas. It was perfect for playing games, chatting and eating together as a family, but also having enough space to do individual things and still be together. Thank you so much for making this lovely home available! We will definitely be returning!
Stayed 7 nights in Jul 2024

10/10 Excellent

Bruce P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful river house
This place was awesome! Though the weather was a bit hot, we still enjoyed our time here. The layout was perfect as everyone had their own bedroom with their own bathroom. The views are stunning both inside and out.
Stayed 4 nights in Jul 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay!
Overall very impressed with the property. This was the perfect stay for our little family getaway. House itself has everything you could need. We cooked in two nights and had no problem given the fully stocked kitchen and outdoor grill. Rooms were great, updated bathrooms and comfy beds. Location is prime. Great view from the large windows on the main floor and walkable to downtown Chestertown. Overall would 100% stay here again!!
Stayed 3 nights in Jun 2024

10/10 Excellent

Pam S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relaxing with friends
We hand a wonderful time enjoying your beauutiful home. It is even better than the pictures. Everything was perfect and not having to bring sheets and towels was an added bonus. The view is lovely and the house is close to everything. We will most definitely be back. Peter was a pleasure to deal with.
Stayed 4 nights in Jun 2024

10/10 Excellent

James K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House, Great Location
Spent a lovely Memorial Day weekend here with two other families (9 people total). The house was just as advertised. Easy walk into charming Chestertown and so many spaces to relax and unwind. The beds were all very comfortable and the kids really loved their bunk bed room. Plenty of cookware, stemware, etc. Would definitely go back!
Stayed 3 nights in May 2024

10/10 Excellent

deb v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Extremely well-appointed and simply gorgeous!
We were six adults (no children), including two elderly parents. The home has stunning views, a fantastic screened great room, and a first-floor primary suite, perfect for our parents. They also had easy access to all the amenities on the property. (There are a few steps from the driveway to the house, but it was manageable for them.) The kitchen is very well equipped, and the layout of the main living areas is lovely, with several areas inside and out to gather as a larger or smaller group. You could tell this was a thoroughly planned home, and they did an excellent job creating a high-end yet comfortable retreat. If you like board games there are dozens available too. We used the fire pit but were not prepared to use the hot tub because we thought it would be closed through May due to the VRBO listing info. Some tiny paver ants were around the kitchen island, but nothing to warrant avoiding the property, probably because it was a change of season. I hope to return as it was likely the most well-appointed rental property I have ever stayed at! Highly recommended.
Stayed 3 nights in Apr 2024

10/10 Excellent

Rod I.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect retreat home
This place was magnificent! Though the weather was a bit cold with some rainy days, it was such a beautiful place to look out in to the river while in the kitchen area and having some much needed family time! Thank you to the owner who's very friendly.
Stayed 7 nights in Mar 2024

10/10 Excellent

Carter F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful river home
Well maintained and equipped. Great for gathering of friends and family
Stayed 2 nights in Jan 2024

10/10 Excellent

Sheila C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Most Wonderful Place to stay at this Magical Time of Year
Everything was so perfect. My husband sister brother and my fav family from C Town all gathered for 2 nights at the "C Town Christmas Cottage" as I now call it. Everything exceeded expectations. Especially the views. We got up early to watch the fog roll onto the inlet. It was exciting, relaxing, and thrilling all at one time. I can not put into words just how special it was. We will be back to drink coffee and champagne on the back deck. The indoor/outdoor space was so incredible. It makes the gathering area even more wonderful.
Stayed 2 nights in Dec 2023

10/10 Excellent

Jennifer S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanksgiving Weekend
We stayed at the cottage over Thanksgiving and it was the perfect place to be with family of all ages. The kitchen was very well appointed. The living space was comfortable and spacious, with the added bonus of a console full of games and puzzles. The views were beautiful and the porch and deck added additional places to hang out and enjoy the scenery. The beds were very comfortable and the ensuite baths afforded everyone their our privacy and space. We will definitely be back when it's warmer to enjoy the pool and water activities.
Stayed 2 nights in Nov 2023

10/10 Excellent

Mark M., Anne arundel county

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beauty on the river
Great all around
Stayed 2 nights in Nov 2023

10/10 Excellent

Sue

Liked: Cleanliness, check-in, communication, location, listing accuracy
Magical weekend
We came for a family reunion during Downrigging Weekend and stayed 4 nights. Breathtaking views from all rooms, very generous common spaces and comfortable bedrooms all with attached baths. The pictures online cannot begin to showcase how fantastic this property is. Every space in the house is so well thought out, up to date, and immaculate. Kitchen is extremely well equipped for real cooking. We also enjoyed s’mores over the fire pit on the spacious deck and loved watching the tall ships sail past all weekend. Easy trips into town for all the festivities. Other family members that stayed in other accommodations were very jealous! Cannot recommend highly enough!
Stayed 4 nights in Oct 2023

10/10 Excellent

David S., Springfield VA

Liked: Cleanliness, check-in, communication, location, listing accuracy
A truly lovely river house
This place is a stunner. Beautiful views in all directions, very private setting, incredibly well equipped. The house is very comfortable. We spent most of our time on the screened in porch or in the large wonderful pool. But paddle boarding and kayaking were on the agenda. And get this...a rental home where EVERYTHING works as it should--the pool, the hot tub, the gas grill, the fire pit, and the appliances. Communication with the owner was excellent. In other words, perfect.
Stayed 6 nights in Aug 2023

10/10 Excellent

Mary R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolute Five Star Experience
We could not have been more pleased with our stay at this lovely home on the Chester River! The home is gorgeous, incredibly well equipped, located spectularly on the water, and even has a beautiful built in swimming pool. We are unfortunately outgrowing the property as our grown children have children of their own. But undoubtedly some subset of us will return again and again! Thank you for a lovely vacation!
Stayed 6 nights in Aug 2023

10/10 Excellent

SHERRRY C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Scenic water views/ made for families
Everyone in our three families thoroughly enjoyed the house and property and felt that it was perfect for us. We had 2-6 year olds, 2-9 year olds, 4-40 somethings and 2-70 somethings. The kids totally enjoyed fishing from the pier and riding the paddle boards and kayaks.(so did the adults). The pool was great and the house had all the necessary amenities to make it a very comfortable stay. We enjoyed the fact that it was not too far from town that you could walk in or go in just to look around, shop, or get ice cream. We look forward to returning in the future.
Stayed 4 nights in Jul 2023

10/10 Excellent

David K., Fairfax, Virginia

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect summer getaway for a large family
Thank you Peter for an awesome property that has it all. My family of 10 from age 5 to 70 enjoyed a relaxing 4-night stay at the cottage. We rarely left the property as we could grill, swim, stand-up paddle boat, kayak, fish, play cornhole, cook, eat, and relax all without leaving. The cottage has an Xbox in the kids room and a large selection of board games. There are binoculars for nature watching. There is a gas fire pit on the dock-side porch which also has a screened-in area. The kitchen has everything you need to cook and serve up meals; just bring the ingredients. The only thing is the sun gets very hot by the pool. So we're glad we brought a shelter for shade. A good thing to remember if staying in the hot months. If you need to venture out, Chestertown has a park with a playground and trail, walking distance away. A bread company/cafe is a few blocks from from the park with excellent pastry and coffee. ACME grocery is another 5 minute drive and ACME's parking has a EV fast-charging station. All in all, a flawless property and we hope to find the time to come back for another stay.
Stayed 4 nights in Jul 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Girls trip in Chestertown
My friends and I stayed here for a girls trip over Memorial Day Weekend and couldn't have been happier. The house (or cottage as the family calls it) is so charming and homey. The entire house was so clean and well taken care of. The beds were comfy and we loved the open concept on the main floor. The kitchen had everything we could have possibly needed to cook. The pool and hot tub were clean and properly heated. The dock was also such a nice treat- we loved having our coffee in the morning and s'mores by the fire at night. Lastly, the host, Peter was so accommodating and easy to communicate with. This house has everything you could possibly need and want to have an amazing weekend on the water. It's rare to show up to a rental property that blows your expectations out of the water and this house did just that! Can't wait to return.
Stayed 3 nights in May 2023

10/10 Excellent

Jennifer H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing water views
Came with a my brothers and nephews for hunting trip. House was perfect. We had a blast
Stayed 2 nights in Jan 2023

10/10 Excellent

Patricia D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Family Gathering
Our family thought the house was absolutely perfect for entertaining. Plenty of seating inside and out. The house flows beautifully with a spacious sunroom that becomes part of the living space by opening glass sliders. This home is very well appointed. You will not need to worry about kitchen utensils, paper product, linens, towels at all. Our stay was in November, so we cannot review the pool or water sport activities on the river. We did enjoy sunrise and sunset river views along with nightly fire pit chats on the dock deck. We will probably be booking another stay here in the future.
Stayed 3 nights in Nov 2022

10/10 Excellent

Brett A., WASHINGTON, DC

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just perfect!!!
Absolutely wonderful. Of all the houses we’ve rented as an extended family over the years, this is probably the best combination of stunning view, functional for a large family, cozy, and right next to a beautiful town with activities. The decor and appointments are wonderful and the beds are a dream. Everyone at every age loved it - the pictures don’t do it justice - it has a whole wall that opens to face the river. Book now before everyone finds out about it!
Stayed 2 nights in Oct 2022

10/10 Excellent

Joseph P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, incredible view
A great location for a family gathering. Very nicely furnished and finished-with lots of space to spread out in. A very short drive to the quaint downtown area of Chestertown—you could certainly walk if you wanted to. Plenty of food options close by, although it’s worth noting that many of them are closed on Mondays. Great communication directly with owner when needed (but only needed for a few minor details.) Last, but not least, the view of the Chester river—literally at your doorstep—was truly impressive. We had a great stay.
Stayed 3 nights in Sep 2022

About the host

Hosted by Peter Heller

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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