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

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Property grounds
On the beach, sun-loungers
Smart TV, fireplace, table football, books
Dining
Exterior

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View 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

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. Plus you'll find laundry facilities and 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 3.1 km (2 mi) from Chestertown Historic District.
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What's nearby

  • Kings Town Park - 3 min drive - 1.8 km
  • Washington College - 4 min drive - 4.2 km
  • Delaware State University - 53 min drive - 66.2 km
  • Dover Downs Casino - 56 min drive - 67.6 km
  • Dover International Speedway - 61 min drive - 67.6 km

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬6 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Dunkin - ‬7 min drive
  • ‪Royal Farms - ‬5 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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  • Dryer
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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

  • 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.
  • 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
Information provided by the property may be translated using automated translation tools

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
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 and laundry facilities, as well as 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. 86 out of 91 reviews
Rating 8 - Good. 5 out of 91 reviews
Rating 6 - Okay. 0 out of 91 reviews
Rating 4 - Poor. 0 out of 91 reviews
Rating 2 - Terrible. 0 out of 91 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Kevin C.

Stayed 2 nights in Apr 2026

10/10 Excellent

Michael F.

Liked: Cleanliness
We love coming here for peaceful getaways of bird watching and quiet days on the river.
Stayed 7 nights in Mar 2026

10/10 Excellent

David J.

Liked: Cleanliness
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

10/10 Excellent

Cory F.

Liked: Cleanliness
Location. Host was commutative and helped with process.
Stayed 3 nights in Jan 2026

10/10 Excellent

Michael F.

Liked: Cleanliness
Even in the darkest days around the winter solstice the beauty of the river at the house is a wonder. We welcomed in a new year by sweating out the old year in the sauna and by communing with the cacophonous geese and the stoic eagles. Wishing all of us new beginnings in 2026!
Stayed 4 nights in Dec 2025

10/10 Excellent

Nick O.

Liked: Cleanliness
Had a wonderful visit! Beautiful home
Stayed 3 nights in Dec 2025

10/10 Excellent

Michael F.

Liked: Cleanliness
We love spending quiet time on the idyllic Chester river. The house is a wonderful getaway.
Stayed 3 nights in Oct 2025

10/10 Excellent

Suzan B.

Liked: Cleanliness
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
Stayed 3 nights in Sep 2025

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 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