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

Beachfront holiday home for sun and fun

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Property grounds - Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! (Chestertown)
Exterior - Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! (Chestertown)
Smart TV, fireplace, table football, books - Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! (Chestertown)
Dining - Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! (Chestertown)
On the beach, sun-loungers - Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! (Chestertown)
Escape to this private paradise on the Chester River, where you can unwind with breathtaking sunsets and stargaze by the fire pit. Enjoy activities like crabbing, fishing, or kayaking from your 200+ foot private beach. This three bedroom home features a master bedroom with French doors overlooking the river and two common areas with glass doors offering spectacular views of the shoreline.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 10

Popular amenities

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

Add dates for prices

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 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

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  • Washing machine
  • Dryer
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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 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

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

Property is also known as

Vrbo Property

About the area

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 Crumpton Auction and Hazel Miner Monument. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Visit our Chestertown travel guideOpens in a new window
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Map
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

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

Restaurants

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

How much is parking at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

On-site parking is available at the property.

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!?

Checkout is at 11:00 AM.

Where is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! located?

Located in Chestertown, this beachfront holiday home is in the city centre and within 3 mi (5 km) of Kings Town Park, Roundtop Park and Chestertown Historic District. Wilmer Park and Rolling Road Park are also within 3 miles (5 km).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 81 out of 86 reviews
Rating 8 - Good. 5 out of 86 reviews
Rating 6 - Okay. 0 out of 86 reviews
Rating 4 - Poor. 0 out of 86 reviews
Rating 2 - Terrible. 0 out of 86 reviews

9.8

Cleanliness

10

Location

Reviews

10/10 Excellent

Andrew M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Location

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

10/10 Excellent

Jason S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

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

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

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

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

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

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

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

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing

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

10/10 Excellent

Adam B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Linda E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

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

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

Karin C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Elyce R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

8/10 Good

Debbie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Betsy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

Suzan B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

victoria g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

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

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

Carter F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

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

Amy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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