See all properties
Save
Entire home

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

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

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

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Beach view
  • Washer
  • Pet-friendly
  • Parking available
  • Outdoor space
  • Air conditioning

Explore the area

Map
Chestertown, MD
  • Historical Society of Kent County Maryland
    ‪5 min drive‬
  • River Arts Chestertown
    ‪5 min drive‬
  • Washington College
    ‪6 min drive‬
  • Baltimore, MD (MTN-Martin State)
    ‪106 min drive‬

Room options

About the area

Chestertown

A family-friendly stay in the heart of Chestertown awaits you at this holiday home. You'll be 1.9 km (1.2 mi) from Kings Town Park and 3 km (1.8 mi) from Roundtop Park. Highlights at this beachfront holiday home include a kitchen, a washing machine and free WiFi. .Home features 2 bathrooms, a fireplace and a living room. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A Smart TV, a coffee/tea maker and a hairdryer are also available. .Spend the day at the beach where you'll find sunloungers, and enjoy the on-site sauna. Additionally, you'll find a garden. .With a stay at this Chestertown holiday home, you'll be 3.1 km (1.9 mi) from Historical Society of Kent County Maryland and 3.2 km (2 mi) from Garfield Center for the Arts at the Prince Theater.
View more Holiday homes in ChestertownOpens in a new window

What's nearby

  • Historical Society of Kent County Maryland - 5 min drive - 3.1 km
  • Garfield Center for the Arts at the Prince Theater - 5 min drive - 3.2 km
  • River Arts Chestertown - 5 min drive - 3.5 km
  • Washington College - 6 min drive - 3.7 km
  • Rolphs Wharf Marina - 12 min drive - 7.9 km

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

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

Similar properties

Interior

Pet-Friendly Home on Chester River w/ Dock!

  • Pool
  • Kitchen
  • Pet-friendly
  • Air conditioning
4.8 out of 5, Exceptional, 4 reviews
Pet-Friendly Home on Chester River w/ Dock!

Property amenities

Beach

  • On the beach
  • Beach loungers

Pool/Spa

  • Sauna

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

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

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Firepit
  • Garden
  • Outdoor furniture
  • Porch/lanai

Laundry

  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

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

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Bicycles
  • Foosball table
  • Kayak
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

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

General

  • Bicycles
  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in and check-out are 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 are welcome
  • Only dogs are allowed
  • Maximum 2 pets
    • Service animals are exempt from fees.
  • 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
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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a smoke detector in all accommodation.

Property is also known as

Vrbo Property

Frequently asked questions

Are there any beaches close to Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

The closest beach to Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! is Betterton Beach (17.4 km).

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! have a pool?

No, this holiday home doesn't have a pool.

What luxury perks are available at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

This property features a sauna, as well as a fireplace and a living room.

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

You bet! With amenities such as a playground, children's books and travel cots, it's no surprise that Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! is a winner with our family travellers.

Is there a free airport shuttle available at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

No, Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! does not offer an airport shuttle service.

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

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 71 out of 76 reviews
Rating 8 - Good. 5 out of 76 reviews
Rating 6 - Okay. 0 out of 76 reviews
Rating 4 - Poor. 0 out of 76 reviews
Rating 2 - Terrible. 0 out of 76 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Coleen M., New Jersey

Liked: Cleanliness
Stayed 3 nights in Feb 2025

10/10 Excellent

Carter F.

Liked: Cleanliness
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

10/10 Excellent

karen m.

Liked: Cleanliness
Stayed 2 nights in Dec 2024

10/10 Excellent

Michael F.

Liked: Cleanliness
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

10/10 Excellent

Linda E.

Liked: Cleanliness
Chester River Home
This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.
Stayed 4 nights in Oct 2024

10/10 Excellent

Jason S.

Liked: Cleanliness
Great
Very beautiful views and relaxing. Our dog loved it too.
Stayed 2 nights in Sep 2024

10/10 Excellent

Karin C.

Liked: Cleanliness
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

Verified traveller

Liked: Cleanliness
Relaxing
Only two days but it was scenic and relaxing on the water.
Stayed 2 nights in Sep 2024

10/10 Excellent

Pat O.

Liked: Cleanliness
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

Cindy D.

Liked: Cleanliness
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

Suzan B.

Liked: Cleanliness
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

Bryn M.

Liked: Cleanliness
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

Michael F.

Liked: Cleanliness
Always a delight!
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
Stayed 7 nights in Mar 2024

10/10 Excellent

Michael C.

Liked: Cleanliness
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

Madeleine S.

Liked: Cleanliness
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

Maria S.

Liked: Cleanliness
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

8/10 Good

Debbie F.

Liked: Cleanliness
Not exactly as pictured
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
Stayed 3 nights in Sep 2023

10/10 Excellent

Karin C.

Liked: Cleanliness
Just what we were looking for
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
Stayed 3 nights in Sep 2023

10/10 Excellent

Adam B.

Liked: Cleanliness
Wedding Weekend
Our adult family stayed for the weekend to attend a nearby wedding. Property is expansive with all the amenities that you can imagine. House is clean, well equipped and beautifully situated. I highly recommend.
Stayed 2 nights in Sep 2023

10/10 Excellent

Elyce R.

Liked: Cleanliness
Amazing Family Vacation in Chestertown
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
Stayed 7 nights in Aug 2023

10/10 Excellent

Michael F.

Liked: Cleanliness
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

Melanie B.

Liked: Cleanliness
Perfect getaway spot
My two young kids loved swimming in the river. One has sensory needs and enjoyed the muddy waters immensely. The house was nicely set up to give my family of four and my mother in law a little privacy in the evenings. Would recommend and come again. Communication with hosts easy and prompt.
Stayed 3 nights in Jul 2023

10/10 Excellent

Patricia D., Warrington, PA

Liked: Cleanliness
Chestertown rental
Great house, beautiful waterfront property!
Stayed 7 nights in Jul 2023

10/10 Excellent

Crystal P.

Liked: Cleanliness
Beautiful Place
This home was a lovely place to stay and relax. Very charming. Beautifully decorated but still comfortable. After 3 days in D.C., this was a great getaway. If we get back to the Maryland area, will likely stay here again if available. ❤️
Stayed 3 nights in Jun 2023

10/10 Excellent

Kathryn W.

Liked: Cleanliness
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