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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

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Chestertown, MD
  • Place, Wilmer Park
    ‪14 min walk‬
  • Place, River Arts Chestertown
    ‪1 min drive‬
  • Place, Washington College
    ‪2 min drive‬
  • 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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House Rules

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

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
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 cycling and ecotours.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Wilmer Park - 14 min walk - 1.2 km
  • River Arts Chestertown - 1 min drive - 1.7 km
  • Historical Society of Kent County Maryland - 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
  • ‪Procolino's - ‬4 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 4 May, 2026, prices found for a 1-night stay for 2 adults at Breathtaking waterfront home on the Chester River on 26 May, 2026 start from S$1,050, 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 38 out of 39 reviews
Rating 8 - Good. 1 out of 39 reviews
Rating 6 - Okay. 0 out of 39 reviews
Rating 4 - Poor. 0 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Beth W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Apr 2026
Verified

10/10 Excellent

Sheila C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Claire F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful stay at a beautiful home

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.
Stayed 4 nights in Jun 2025
Verified

10/10 Excellent

Colleen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip by the water

We try to take an annual family trip that involves water activities. This house and property was the perfect spot for our family which includes young children.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

James K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Great Stay

Two years in a row we've had an incredible Memorial Day weekend at this house. Tons of room for everyone, the river views are fantastic and the pool area is very relaxing. Also helps that it's a very easy bike ride into Chestertown. Highly recommend this place.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

JAMES C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Downrigging!

Great place and great stay!
Stayed 2 nights in Nov 2024
Verified

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
Verified

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
Verified

10/10 Excellent

jacob s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous place!

The house is beautiful, with a glorious glassed-in porch perched over the river. Ideal space for a family reunion. You couldn't ask for a better place on the river.
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

Brian O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So Relaxing

The listing was exactly as described. It also was very clean and well stocked. It is probably the best stocked VRBO I have ever stayed in. The views were amazing, the pool was great, and we couldn't have asked for anything better. Peter was a great host and was easy to communicate with. He even provided dinner recommendations.
Stayed 7 nights in Aug 2025
Verified

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
Verified

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
Verified

10/10 Excellent

Bijoy V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Aug 2025
Verified

8/10 Good

Sheila C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Magical as Ever

We loved our stay as much as we did last year. We were there for 5 nights and celebrated Christmas with friends and extended family. The views from every room were spectacular. From breakfast to midnight snacks we enjoyed the river and the cozy stove while watching Christmas classics and playing all the games Santa brought us.
Stayed 5 nights in Dec 2024
Verified

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
Verified

10/10 Excellent

kate k.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls weekend

The cool weather kept us indoors playing games, puzzles, drinking wine and eating great food we picked up at the farmers market. Took a while for the hot tub to heat up but it was wonderful.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Mark M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beauty on the river

Great all around
Stayed 2 nights in Nov 2023
Verified

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
Verified

10/10 Excellent

Kimberly D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home, peaceful & quiet with lovely lapping water sounds and bird chirping. Our family of 9 (6 adults/3 active children) enjoyed all the amenities of swimming in the pool/river, kayaking, fishing from the pier, enjoying family meals together, exploring the lovely town 5 min away with the shops and nice playground by the waterfront. Sunrise and sunsets are gorgeous! Management is excellent and responsive to requests, etc. Definitely 10 thumbs up!
Beautiful sunrise from the pier!
Stayed 7 nights in Jul 2025
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Margaret B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome riverside cottage with panorama views from every room

We can’t overstate what a great find this was. In addition to the lovely setting, the cottage was well equipped, the kitchen but also with games, art and craft supplies and puzzles for kids. We think in summer with the pool and river to enjoy it would be even better. We are grateful to the owners for being willing to share this treasure!
Stayed 3 nights in Nov 2024
Verified

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
Verified

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

About the host

Hosted by Peter Heller

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Languages:

English

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