Entire home

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

Beachfront holiday home with kitchen and fireplace

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

Exterior
Sauna fits 6 people but comfortably 4 if you need more space.
Beach
Pool
Living area

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • Dryer
  • Fireplace
  • Washer
  • Beach view

Explore the area

View 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

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bunk Bed and 1 Queen Bed

Bedroom with river view

1 King Bed and 2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Outdoor play area
Garden

About this property

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**

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 2 total)
Please do not allow your pets on the furniture.
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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

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the beach. Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Travelling with kids? Consider Crumpton Auction and Hazel Miner Monument. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 5 min drive - 3.2 km
  • River Arts Chestertown - 5 min drive - 3.5 km
  • Washington College - 5 min drive - 3.8 km
  • Chestertown Dog Park - 7 min drive - 5.2 km
  • Rolphs Wharf Marina - 13 min drive - 8.3 km

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

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!?

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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 78 out of 83 reviews
Rating 8 - Good. 5 out of 83 reviews
Rating 6 - Okay. 0 out of 83 reviews
Rating 4 - Poor. 0 out of 83 reviews
Rating 2 - Terrible. 0 out of 83 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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

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

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

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

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

10/10 Excellent

Eve F.

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

June wedding weekend

A seamless experience from start to finish. We were pleased with the space and amenities.
Stayed 2 nights in Jun 2022

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

Morag B.

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

Beautiful place

Beautiful house, great location. Our family- aged 9 to 93 had a great time and would love to return. Our only issue was the listing didn't mention that you need to bring your own sheets, towels and toilet paper, which would have been good to know before we got our check-in email.
Stayed 3 nights in May 2021

10/10 Excellent

Emily L.

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

Everything you could want

Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
Stayed 3 nights in May 2023

10/10 Excellent

Jenifer H.

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

Peaceful, relaxing property!

My family and I enjoyed a few days of relaxation while we watched the water, some boaters, and wildlife through the many glass doors (we had a very hot few days). We were also able to enjoy the kayak and fire pit. The home was clean and spacious. There are plenty of areas to spread out or gather together for games. We enjoyed our stay.
Stayed 4 nights in Aug 2022

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

Verified traveller

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

Beautiful house by the river

My best friend and I had a great time at this beautiful house! The interior is lovely, with plenty of open space and an awesome foosball table. : ) The back yard, pier and fire pit are a fantastic place to relax - as is the screened-in porch, where we spent most of our time. Many thanks to Ina and Mynor!
Stayed 2 nights in May 2022

10/10 Excellent

Kimberly B.

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

Great long weekend on the eastern shore!

The property was exceptionally well-appointed, from the kitchen equipment to the outdoor equipment (kayaks. paddle boards, bikes, etc.). We enjoyed the firepit by the water and used the dock for some very successful fishing! We will be back for sure :)
Stayed 4 nights in Sep 2022

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

Michael F.

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

Idyllic River Retreat

We spent countless hours on the screened in porch gazing out at the idyllic landscape. Every day we saw the bald eagles, osprey and cormorants fishing in the river, and once the sun set we were visited by a parliament of three juvenile barred owls hunting their prey. It is a wonder how watching the birds heals the soul. We enjoyed wading and swimming in the river, and our 17-month-old dog Sadie learned to love the water. By mid-vacation she was swimming like a pro. She even proved to be an ardent kayaker and would jump into the front of the two man kayak and let one of us paddle her around like Cleopatra on the Nile. The house is just the perfect size to be cozy while having every amenity we could need. Chestertown, particularly the Saturday Farmer’s market, is a true hidden gem.
Stayed 12 nights in Aug 2021

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

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

John P.

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

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

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

About the host

Hosted by Ina Herrera

Host profile image
Being able to provide our renters with a place to relax and rejuvenate is our goal, the way it does for us when we visit with our own family.

Languages:

English, Spanish, Norwegian

Premier Host

They consistently provide great experiences for their guests