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

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

Terrace/patio
Miscellaneous
Smart TV, fireplace, foosball, books
Fridge, microwave, oven, stovetop
Property grounds

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Washer
  • Beach view
  • Pet friendly
  • Parking available
  • Outdoor Space
  • Air conditioning

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end throughout the year. The home is also located just a short bike ride to Historic Chestertown, or you can even take one of our kayaks in while you enjoy the Chester River's rich wildlife.

Guests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings.

The three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun.

Minutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!

Chestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food.

About 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River.

With so many things to enjoy, book your experience today!

**Sheets are provided and beds made, but please bring towels**

Property manager

Ina Herrera

Languages

English, Norwegian, Spanish

Property amenities

Beach

  • On the beach
  • Beach sun loungers

Pool/Spa

  • Sauna

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Toaster
  • Ice maker
  • Cookware/dishes/utensils
  • Coffee/tea maker

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shower
  • Toilet paper
  • Hair dryer
  • Soap

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite service
  • Foosball table
  • Books
  • Games

Outdoor areas

  • Porch or lanai
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total pets
  • Welcoming dogs only

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair accessible
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • On the river
  • On the waterfront
  • In the city center
  • In a rural location
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping
  • In a village

Things to do

  • Fitness facilities nearby
  • Kayak on site
  • Bicycle on site
  • Marina nearby
  • Kayaking nearby
  • Hunting nearby
  • Hiking/biking trails nearby
  • Sailing nearby
  • Hiking nearby
  • Ecotours nearby
  • Birdwatching nearby
  • Fishing nearby

Safety features

  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector or gas appliances on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)

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Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Note from host: Please do not allow your pets on the furniture.

Children and extra beds

Children are welcome

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
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Vrbo Property

About the neighborhood

Map
Chestertown, MD

What's nearby

  • Kings Town Park - 4 min drive
  • Historical Society of Kent County Maryland - 5 min drive
  • River Arts Chestertown - 5 min drive
  • Washington College - 6 min drive
  • Rolphs Wharf Marina - 12 min drive

Getting around

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

Restaurants

  • ‪McDonald's - ‬7 min drive
  • ‪Dining Hall - ‬7 min drive
  • ‪Procolino Pizza - ‬7 min drive
  • ‪China House - ‬7 min drive
  • ‪The Freeze - ‬7 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).

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 Wilmer Park. Rolling Road Park and Historical Society of Kent County Maryland are also within 3 mi (5 km).

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

Reviews

10

Exceptional

Rating 10 - Excellent. 70 out of 75 reviews
Rating 8 - Good. 5 out of 75 reviews
Rating 6 - Okay. 0 out of 75 reviews
Rating 4 - Poor. 0 out of 75 reviews
Rating 2 - Terrible. 0 out of 75 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Shaun S., Del Mar

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was perfect
Loved our stay!
Stayed 3 nights in Oct 2021

10/10 Excellent

Hardeep S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and hours
Enjoyed our stay here
Stayed 2 nights in Jan 2022

10/10 Excellent

Bryn M.

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

10/10 Excellent

Cindy D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Place on the River in Chestertown
We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!
Stayed 2 nights in May 2024

10/10 Excellent

Karin C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved it
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
Stayed 3 nights in Sep 2024

10/10 Excellent

David D.

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

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice house on a beautiful river front property
We had a fantastic get together with friends and family. Highly recommended.
Stayed 4 nights in Feb 2024

10/10 Excellent

Suzan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Relax, Recharge & Reconnect
This was the perfect place to gather our family of 5 adults and our 3 fur babies to celebrate Mother’s Day over the weekend. The house is beautifully decorated and we thoroughly enjoyed the large property that was very private and had not only access to the water but also stunning views. We look forward to coming back.
Stayed 2 nights in May 2024

10/10 Excellent

Madeleine S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Chestertown Getaway
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
Stayed 2 nights in Dec 2023

10/10 Excellent

Andrew E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and nice house
Lovely setup on the water
Stayed 4 nights in Jan 2023

10/10 Excellent

Sean & Jasmine R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent peaceful scenic stay
We enjoyed a peaceful getaway, with beautiful sunsets, and a cozy setting. Will definitely do again.
Stayed 3 nights in Aug 2021

10/10 Excellent

Emily L.

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

10/10 Excellent

Doug B., ALEXANDRIA

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great to work with owners
Wonderful in all aspects! Looking forward to our next stay!
Stayed 2 nights in Jul 2021

10/10 Excellent

Debbie R.

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

10/10 Excellent

Michael F.

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

10/10 Excellent

Patricia D., Warrington, PA

Liked: Cleanliness, check-in, communication, location, listing accuracy
Chestertown rental
Great house, beautiful waterfront property!
Stayed 7 nights in Jul 2023

10/10 Excellent

Kathryn W.

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

10/10 Excellent

Pat O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Vacation
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
Stayed 8 nights in Jun 2024

10/10 Excellent

Lynda M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Listing
The illuminated pier at night was a treat!
Stayed 4 nights in Feb 2023

10/10 Excellent

kathy g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect Get-Away
Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown
Stayed 4 nights in Apr 2023

10/10 Excellent

Maria S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanksgiving Retreat
Wonderful weekend with our daughters. Chester town was festive kicking off the holidays with a parade. This is our second trip to an area on the Eastern Shore and it did not disappoint. The home was lovely and a relaxing environment.
Stayed 2 nights in Nov 2023

10/10 Excellent

Aloise B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, clean property on the Chester River
The property is beautiful with lots of toys (paddleboards, kayaks, etc.) for guests to use. The house was very clean. Everyone in my family enjoyed our stay here.
Stayed 4 nights in Jul 2022

10/10 Excellent

Lisa V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Summer Vacation
We had a great family trip. The location is perfect and was very peaceful. The house had lots of games for kids and was very comfortable. We will stay again.
Stayed 6 nights in Jul 2022

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
An escape to a peaceful river getaway
We have visited Ina’s house on the Chester river several times. It is a serene and peaceful sanctuary perfect for watching the birds and kayaking amongst the reedy shores. A stay here always serves to restore our souls.
Stayed 14 nights in Jul 2023

10/10 Excellent

Betty M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property
Our stay was short, but absolutely fantastic! Great house, stunning view. We will definitely be back it must be even more gorgeous in the summer. ♥️
Stayed 2 nights in Mar 2023