Breathtaking waterfront home on the Chester River

Photo gallery for Breathtaking waterfront home on the Chester River

A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of a body of water.
A spacious living area with a dining table, comfortable seating, a fireplace, and a kitchen with modern appliances.
A modern kitchen with stainless steel appliances, a large island, and a view of the outdoors.
A spacious kitchen with white cabinetry, a central island with stools, and a large window providing natural light.
A living room with a sectional sofa, a coffee table, and a view of the outdoors.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • 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.

Popular amenities

  • Balcony
  • Private pool
  • Barbecue
  • Arcade/game room
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪2 min drive‬
  • Place, Chestertown Historic District
    ‪2 min drive‬
  • Place, Washington College
    ‪2 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪128 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

Add dates for prices

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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 Schooner Sultana and Garfield Center for the Arts at the Prince Theater. Larrabee Arts Center and Crumpton Auction are also worth visiting. Discover the area's water adventures with jet skiing and waterskiing nearby, or enjoy the great outdoors with ecotours and hiking.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Sumner Hall - 17 min walk - 1.5 km
  • River Arts Chestertown - 2 min drive - 1.7 km
  • Chestertown Historic District - 2 min drive - 2.1 km
  • Historical Society of Kent County Maryland - 2 min drive - 2.1 km
  • Washington College - 2 min drive - 2.4 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 108 min drive

Restaurants

  • ‪Royal Farms - ‬5 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Dunkin - ‬4 min drive
  • ‪Procolino's - ‬4 min drive
  • ‪Royal Farms - ‬2 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.

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 Schooner Sultana. Chestertown Historic District and River Arts Chestertown 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. 44 out of 45 reviews
Rating 8 - Good. 1 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect! This place has everything you need.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was the perfect house for our annual summer family week. Between the pool, the dock, the river beach access, the paddle boards and kayak, there was just so much to do. The house is beautifully and tastefully appointed, each bedroom has its own bathroom, and the house was very clean. Communication was quick and easy and we fell in love with the town of Chestertown too! Loved the ability to walk into town but just wished there was more of a pedestrian way on the road into town.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

Wonderful property!

Great house. Perfect location. Wonderful host.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Downrigging!

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

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 6 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Beauty on the river

Great all around
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
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