Entire home
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
3 bedrooms2 bathroomsSleeps 10
Popular amenities
Explore the area

Chestertown, MD
- Place, Baltimore Inner Harbor Marina
- Place, Kings Town Park3 min drive
- Place, Roundtop Park3 min drive
- Airport, Baltimore, MD (MTN-Martin State)110 min drive
Rooms & beds
3 bedrooms (sleeps 10)
Bedroom 2
1 Queen Bed
Bedroom 3
1 Single Bunk Bed and 1 Queen Bed
Bedroom with river view
1 King Bed and 2 Single Beds
2 bathrooms
Bathroom 1
Toilet · Shower only
Bathroom 2
Bathtub · Toilet · Shower only
Spaces
Porch or lanai
Kitchen
Outdoor play area
Garden
About this property
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
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- Hot tub
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (107 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs (limit 2 total)
Please do not allow your pets on the furniture.
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
About the area
Chestertown
Located in Chestertown, this holiday home is in the city centre 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 Larrabee Arts Center. Travelling with kids? Consider Crumpton Auction and The Mainstay. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Chestertown, MD
What's nearby
- Kings Town Park - 3 min drive - 1.8 km
- Roundtop Park - 3 min drive - 1.8 km
- Washington College - 4 min drive - 3.8 km
- Dover Downs Casino - 54 min drive - 63.8 km
- Dover International Speedway - 58 min drive - 64.2 km
Getting around
Restaurants
- Milano's Pizzeria - 6 min drive
- Royal Farms - 5 min drive
- Dunkin - 7 min drive
- McDonald's - 7 min drive
- Royal Farms - 5 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
8 Mar 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 2 nights in Feb 2026
Verified
10/10 Excellent
Nick O.
11 Dec 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nick O.
Stayed 3 nights in Dec 2025
Verified
10/10 Excellent
Cory F.
11 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cory F.
Stayed 3 nights in Jan 2026
Verified
10/10 Excellent
Betsy W.
25 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Betsy W.
Stayed 2 nights in Sep 2025
Verified
10/10 Excellent
Michael F.
27 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Michael F.
Stayed 3 nights in Oct 2025
Verified
10/10 Excellent
Michael F.
2 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy



Michael F.
Stayed 4 nights in Dec 2025
Verified
10/10 Excellent
victoria g.
10 Jul 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend getaway
victoria g.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Shaun S.
26 Oct 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was perfect
Shaun S.
Stayed 3 nights in Oct 2021
Verified
10/10 Excellent
Andrew M.
25 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Location
Andrew M.
Stayed 2 nights in May 2025
Verified
10/10 Excellent
Hardeep S.
30 Jan 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and hours
Hardeep S.
Stayed 2 nights in Jan 2022
Verified
10/10 Excellent
Suzan B.
30 Sept 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Suzan B.
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
David D.
3 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great family spot
David D.
Stayed 2 nights in Mar 2023
Verified
10/10 Excellent
Carter F.
12 Jan 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend with friends
Carter F.
Stayed 2 nights in Jan 2025
Verified
10/10 Excellent
Jason S.
30 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
Jason S.
Stayed 2 nights in Sep 2024
Verified
10/10 Excellent
Sean & Jasmine R.
17 Aug 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent peaceful scenic stay
Sean & Jasmine R.
Stayed 3 nights in Aug 2021
Verified
10/10 Excellent
Doug B.
5 Aug 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great to work with owners
Doug B.
Stayed 2 nights in Jul 2021
Verified
10/10 Excellent
Andrew E.
31 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and nice house
Andrew E.
Stayed 4 nights in Jan 2023
Verified
10/10 Excellent
Bryn M.
22 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend getaway
Bryn M.
Stayed 2 nights in Apr 2024
Verified
10/10 Excellent
Michael F.
27 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Idyllic River Getaway
Michael F.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
Emily L.
19 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place
Emily L.
Stayed 2 nights in Apr 2023
Verified
10/10 Excellent
Debbie R.
10 Nov 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property on the water . House was well equipped -welcoming to guests , great place !!
Debbie R.
Stayed 2 nights in Oct 2022
Verified
10/10 Excellent
Michael F.
22 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Another relaxing stay at this bucolic riverfront getaway
Michael F.
Stayed 3 nights in Apr 2023
Verified
10/10 Excellent
Amy K.
9 Jun 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amy K.
Stayed 2 nights in Jun 2025
Verified
10/10 Excellent
Kathryn W.
30 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great weekend!
Kathryn W.
Stayed 3 nights in May 2023
Verified
10/10 Excellent
Patricia D.
23 Jul 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown rental
Patricia D.
Stayed 7 nights in Jul 2023
About the host
Hosted by Ina Herrera
Being able to provide our renters with a place to relax and rejuvenate is our goal, the way it does for us when we visit with our own family.
Languages:
English, Spanish, Norwegian
Premier Host
They consistently provide great experiences for their guests
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