Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Photo gallery for Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Property grounds
A spacious living room with a large window, a ceiling fan, a sofa with cushions, a coffee table, and a guitar.
A spacious living room with a wooden dining table, blue sofa, and teal chairs.
A wooden cabin with a fireplace, a bench, and a window.
A wooden boardwalk leading to a house with a lit interior, surrounded by trees and a clear sky.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • On the beach
    A rare beachfront property in the area - enjoy direct access to the beach and sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • On beach
  • Dog-friendly
  • Air conditioning
  • Refrigerator
  • Internet
  • Onsite parking available

Explore the area

View in a map
Chestertown, MD
  • Place, Kings Town Park
    ‪3 min drive‬
  • Place, Washington College
    ‪4 min drive‬
  • Place, Dover Downs Casino
    ‪56 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪130 min drive‬

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Bedroom 3

1 Twin Bunk Bed and 1 Queen Bed

Bedroom with river view

1 King Bed and 2 Twin Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Outdoor play area
Garden

Add dates for prices

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About the neighborhood

Chestertown

Located in Chestertown, this vacation home is in the city center and on the beach. 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 Schooner Sultana. Traveling with kids? Consider Larrabee Arts Center and Crumpton Auction. Kayaking and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Vacation Homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Kings Town Park - 3 min drive - 1.8 km
  • Washington College - 4 min drive - 4.2 km
  • Queenstown Harbor Golf - 38 min drive - 45.8 km
  • Delaware State University - 53 min drive - 66.2 km
  • Dover Downs Casino - 56 min drive - 67.6 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • ‪Royal Farms - ‬5 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Dunkin - ‬7 min drive
  • ‪Procolino's - ‬7 min drive
  • ‪Royal Farms - ‬5 min drive

Frequently asked questions

Is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

As of Oct 28, 2026, prices found for a 1-night stay for 2 adults at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! on Nov 1, 2026 start from $482, 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.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Check-in begins at 3:00 PM.

What time is check-out at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Check-out is at 11:00 AM.

Where is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! located?

Located in Chestertown, this beachfront vacation home is in the city center and within 3 mi (5 km) of Kings Town Park, Roundtop Park, and Chestertown Historic District. Wilmer Park and Rolling Road Park are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 92 out of 97 reviews
Rating 8 - Good. 5 out of 97 reviews
Rating 6 - Okay. 0 out of 97 reviews
Rating 4 - Poor. 0 out of 97 reviews
Rating 2 - Terrible. 0 out of 97 reviews

9.8/10

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
Great property, good house and lovely hosts! We had a wonderful vacation!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful view and location on the river! Also a great place for relaxing, swimming and having a very enjoyable family gathering.
Stayed 8 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love coming here for peaceful getaways of bird watching and quiet days on the river.
Stayed 7 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time! The home was laid out perfectly for our group and very clean and well furnished with everything we needed. Coffee seemed to taste better from the coffee bar! We caught crabs and catfish from the dock. We loved the beautiful sunsets and even watching a storm roll in one evening…Thank you for a memorable week
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The river at the height of summer is the best place to take a deep breath and recuperate from the demands of the life. We always find ourselves rapt by the sunsets, the stars, and the birds. Ina is the best host!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It is a delightful property right on the Chester River, very clean, well organized for the week, stocked with everything and anything you could want. The host was extremely friendly and helpful. And Chestertown is a delightful town. We’ll be back.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wonderful visit! Beautiful home
Stayed 3 nights in Dec 2025
Response from VrboOwner on Dec 15, 2025
Thank you Nick. We would love to have you back some day:-)
Verified review

10/10 Excellent

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

Great place and hours

Enjoyed our stay here
Stayed 2 nights in Jan 2022
Response from VrboOwner on Feb 3, 2022
Great to know that you have enjoyed your stay. We hope to see you again next year :)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was great for families and pets. Very accessible waterfront for dogs. It had nice and relaxing fire pit area and outdoor sauna was a fun experience. The house had everything that we needed. Quick responses from host
Stayed 2 nights in Feb 2026
Response from VrboOwner on Mar 23, 2026
Thank you for the kind words. We are so happy you had a nice stay with us, and we welcome you back anytime.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We love spending quiet time on the idyllic Chester river. The house is a wonderful getaway.
Stayed 3 nights in Oct 2025
Response from VrboOwner on Nov 10, 2025
Thank you Michael. We appreciate you, your husband and your four-legged family member always choosing to come back to our River getaway:-) It truly is a paradise for dogs also:-)
Verified review

10/10 Excellent

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

Great family spot

Great place! Would love to stay in the summer when the weather is warmer and enjoy the outdoors. Enjoyed our time there with visiting with family.
Stayed 2 nights in Mar 2023
Response from VrboOwner on Apr 13, 2023
We are so happy you enjoyed our outdoor sanctuary. Please follow us on instagram @herreravacationrentals to see what we are up to:-)
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location. Host was commutative and helped with process.
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

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

Beautiful Location

Great house with an even greater view.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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

Weekend getaway

One of our favorite spots! Never disappoints.
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

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

Great location and nice house

Lovely setup on the water
Stayed 4 nights in Jan 2023
Response from VrboOwner on Feb 2, 2023
Thank you for staying with us. Hope you enjoyed it.
Verified review

10/10 Excellent

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

Weekend with friends

Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

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

Great place

A great place to relax and enjoy the Chester river and surrounding area. Rental has all the amenities. Can’t wait to go back!
Stayed 2 nights in Apr 2023
Response from VrboOwner on Apr 25, 2023
We are so happy you had a great experience. Please come visit us at a different seasons to see how gorgeous it is. In the meantime, follow us at @herreravacationrentals on Instagram for ideas on what to do
Verified review

10/10 Excellent

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

Beautiful property on the water . House was well equipped -welcoming to guests , great place !!

Perfect experience
Stayed 2 nights in Oct 2022
Response from VrboOwner on Nov 28, 2022
Thank you Debbie, this makes us so happy. We hope you come again, and please tell your friends:-)
Verified review

10/10 Excellent

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

Great

Very beautiful views and relaxing. Our dog loved it too.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

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

Weekend getaway

Beautiful home and property! Host was very communicative and even gave suggestions for places to go in town. Would definitely book again.
Stayed 2 nights in Apr 2024
Response from VrboOwner on Apr 23, 2024
Thank for staying with us. We would love to have you again.
Verified review

10/10 Excellent

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

Another relaxing stay at this bucolic riverfront getaway

We have been back to Ina's beautiful house several times and each time is a pleasure. We enjoy the quiet, the birds, the river's ebbs and flows, and the spectacular sunsets.
Stayed 3 nights in Apr 2023
Response from VrboOwner on Apr 25, 2023
We are so happy you had a great experience. Please come visit us at a different seasons to see how gorgeous it is. In the meantime, follow us at @herreravacationrentals on Instagram for ideas on what to do
Verified review

10/10 Excellent

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

Great weekend!

Thank you for sharing your wonderful home with us! Everything was perfect for our stay-we look forward to staying again soon!
Stayed 3 nights in May 2023
Response from VrboOwner on Jun 2, 2023
This makes us so happy. We are looking forward to hosting you again:-)
Verified review

10/10 Excellent

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

Idyllic River Getaway

We have enjoyed our stays here in all seasons, but autumn is particularly beautiful with the leaves changing color and the migratory birds passing through. Such a great breather from city life.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

Chestertown rental

Great house, beautiful waterfront property!
Stayed 7 nights in Jul 2023
Response from VrboOwner on Jul 26, 2023
Thank for staying with us. We would love to have you again.
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