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

Family-friendly beachfront vacation home with free WiFi

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

Terrace/patio
Fridge, microwave, oven, stovetop
Smart TV, fireplace, foosball, books
Dining
Sauna

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Dryer
  • Beach view
  • Washer
  • Fireplace

Explore the area

View in a map
Chestertown, MD
  • Place, Historical Society of Kent County Maryland
    ‪5 min drive‬
  • Place, River Arts Chestertown
    ‪5 min drive‬
  • Place, Washington College
    ‪5 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪59 min drive‬

Room options

About the neighborhood

Chestertown

On the beach.You'll find Kings Town Park and Roundtop Park within 2 miles (3 km) of this vacation home. Historical Society of Kent County Maryland and Chestertown Historic District are also within 3 miles (5 km).
View more Vacation Homes in ChestertownOpens in a new window

What's nearby

  • Historical Society of Kent County Maryland - 5 min drive - 2.0 miles
  • River Arts Chestertown - 5 min drive - 2.2 miles
  • Washington College - 5 min drive - 2.4 miles
  • Chestertown Dog Park - 7 min drive - 3.3 miles
  • Rolphs Wharf Marina - 13 min drive - 5.2 miles

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬6 min drive
  • ‪Royal Farms - ‬5 min drive
  • ‪Royal Farms - ‬5 min drive
  • ‪Dunkin - ‬7 min drive
  • ‪Procolino's - ‬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**

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Property amenities

Beach

  • On the beach
  • Beach loungers

Pool/Spa

  • Sauna

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

  • Laundry facilities
  • 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.
  • Wheelchair accessibility
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • 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 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.

Events

No events allowed

Smoking

Smoking is not permitted

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
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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a smoke detector in each accommodation.

Property is also known as

Vrbo Property

Frequently asked questions

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to the airport?

This vacation home is 73.2 mi (106-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to the beach?

This vacation home is on the beach. Don't forget your sunscreen!

Does Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

No, there is no casino at this vacation home.

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

Check-in begins at 3:00 PM.

Is there free parking at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Free parking is not available at this vacation home.

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

This vacation home does not have a pool.

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

There are no spa services available at this vacation home.

How close is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! to downtown Chestertown?

This vacation home is 1.6 mi away from Chestertown.

Reviews

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

10

Exceptional

9.8/10

Cleanliness
Rating 10 - Excellent. 77 out of 82 reviews
Rating 8 - Good. 5 out of 82 reviews
Rating 6 - Okay. 0 out of 82 reviews
Rating 4 - Poor. 0 out of 82 reviews
Rating 2 - Terrible. 0 out of 82 reviews

Reviews

10/10 Excellent

Betsy W., Winchester, MA

Liked: Cleanliness
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

10/10 Excellent

Jessica S.

Liked: Cleanliness
Stayed 3 nights in Jun 2025

10/10 Excellent

victoria g.

Liked: Cleanliness

Weekend getaway

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

10/10 Excellent

John P.

Liked: Cleanliness

Quiet Retreat in Peaceful Setting

We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
Stayed 4 nights in Jun 2025

10/10 Excellent

Amy K.

Liked: Cleanliness
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
Stayed 2 nights in Jun 2025

10/10 Excellent

Andrew M.

Liked: Cleanliness

Beautiful Location

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

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 traveler

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