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Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Photo gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

A wooden pier with a white chair and a bird statue.
A garden with orange flowers and a large tree.
A backyard with a swimming pool, a wooden fence, and a flag.
A living room with a fireplace, a round coffee table, a sofa, a leather armchair, and a TV.
A white house with a brick chimney, surrounded by a well-maintained lawn and trees.

Reviews

10 out of 10
Exceptional

Highlights

  • Wildlife at your doorstep
    Guests love spotting wildlife right on the property grounds.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Your private hideaway
    Guests love the secluded location for peace and quiet.
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Private pool
  • Dog-friendly
  • Dock
  • Barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪13 min drive‬
  • Place, Chestertown Historic District
    ‪14 min drive‬
  • Place, Washington College
    ‪14 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪120 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Bathtub or shower · Bathtub · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Garden

About this property

Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.

Modern cottage on tranquil large grounds on 20 acres with a pond on one end and a half mile wide creek 800 feet away on the other with a 100 foot dock. Inside a larger historic 18th century farm with original house and buildings. Expansive views. See beautiful sunsets, birds, deer and more. The salt water pool is shared only with the main house on certain dates in the summer. Guests will have the pool area 6 hours a day to themselves (to Oct 1). Recently renovated and furnished. Outside back yard seating and eating area with BBQ. High speed fiber internet, smart TVs. 2 fat tire bikes available. Central AC and heat. Seating on dock and water with fire pit. Easy access, parking, ground floor Master.

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House Rules

Check in after 2:00 PM
Minimum age to rent: 30
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)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Place keys back in lock box
Set thermostats to 80 in summer and 65 in winter.
Place used towers and sheets in laundry area.
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 2935955vb
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 is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Chestertown

Located in Chestertown, this cottage is on the waterfront. Sumner Hall and Garfield Center for the Arts at the Prince Theater are cultural highlights, and travellers looking to shop may want to visit Chestertown Farmers Market and Queenstown Premium Outlets. Schooner Sultana and Larrabee Arts Center are also worth visiting. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with hunting and cycling.
View more Cottages in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Wilmer Park - 13 min drive - 14.9 km
  • River Arts Chestertown - 13 min drive - 15.5 km
  • Chestertown Historic District - 14 min drive - 15.9 km
  • Historical Society of Kent County Maryland - 14 min drive - 15.9 km
  • Washington College - 14 min drive - 16.6 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 118 min drive

Restaurants

  • ‪Harbor Shack - ‬36 min drive
  • ‪Admiral’s Club Beachside Bar - ‬36 min drive
  • ‪Ford's Seafood - ‬32 min drive
  • ‪Chester River Seafood - ‬37 min drive
  • ‪Waterman's Crab House - ‬34 min drive

Frequently asked questions

Does Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. have a pool?

Yes, this property has an outdoor pool.

Is Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.?

On-site parking is available at the property.

What time is check-in at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.?

Check-in begins at 2:00 PM.

What time is check-out at Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.?

Checkout is at 11:00 AM.

Where is Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock. located?

Situated on the waterfront, this cottage is within 9 miles (15 km) of Wilmer Park, Schooner Sultana and River Arts Chestertown. Chestertown Farmers Market and Sumner Hall are also within 9 miles (15 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. 9 out of 9 reviews
Rating 8 - Good. 0 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Quiet Retreat

lovely grounds
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Best little cottage

So delightful
Stayed 2 nights in Nov 2024
Verified review

10/10 Excellent

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

Top quality

Delightful spot. Well supplied lodging. Many acres of beautiful land and water. Rich variety of wildlife.
Stayed 11 nights in May 2024
Response from VrboOwner on 3 June 2024
Thank you Adrian, hope to see you back!
Verified review

10/10 Excellent

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

Lovely

This was our second stay in the cottage on this beautiful, serene property. If you are looking for comfortable and quiet but the option to go to town for dinner this is the place for you. I know we will be back!
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

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

A true gem!

This property was so much more than anticipated! Beautiful lawn, acres as far as you an see, secluded, private and very relaxing! Robert handled all our needs and was kind enough to share history about the property. We will be sure to visit again!
Stayed 4 nights in Jul 2025
Response from VrboOwner on 25 July 2025
Thanks for your kind review. We enjoy it when people appreciate and share our perspective!
Verified review

10/10 Excellent

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

Serene Getaway

Our stay at the Beatrix Cottage in Chestertown was just perfect. It is in a serene and secluded area with lots of wildlife and natural beauty. The dock area allowed for beautiful sunset views. The saltwater pool was perfect and plenty of time was offered to use it while sharing with the owners. Communication with the owner was excellent and all issues were addressed promptly. This was the perfect quiet getaway for my family. I highly recommend this idyllic spot.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location was beautiful and quiet. A true Shore stay in an out-of-the-way spot. Loved the local wildlife and access to the dock. Pool availability was a plus. Plenty of space for a family. Easy and responsive communication with the host. Thank you!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We (my husband and I and our adult daughter) as well as our three dogs (Nemecsek, the greyhound, Reka, the Irish Doodle, and Wilbur, the mutt) enjoyed our stay at this cottage. It is relly pretty and well equipped, including a wonderful set of blue dishes and pots and pans. The kitchen equipment was so good that we hardly ate out, but rather cooked locally sourced seafood at the cottage. Robert, our host, was very nice and responded to an unexpected emergency with grace and patience. The salt-water pool was an added bonus and the human swimmers in the pack enjoyed it a lot. The sunsets at the waterfront were spectacular. Lots of wild life (deer, frogs, lizards, etc). Got a couple of bug bites while walking the prperty but nothing that a bit of Cortizone wouldn't cure. I highly recomment this property.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jun 2025

About the host

Hosted by Robert

Host profile image
We are from Florida. We love the water and open spaces and this gives us both. At the same time, we have all the convenience of being close to town. We enjoy having people around that appreciate the tranquility, the animal life and the countryside.

Why they chose this property

In this neighborhood, there’s always something to do all year round. Boating and crabbing in the summer, there are multiple activities nearby and beautiful views.

What makes this property unique

This is a historic farm from the late 1700s. The main house nearby from 1781 is in unique condition Inside and out. The grounds are kept up professionally. The waterfront offers a beautiful perspective over a major creek and the sunsets are spectacular.

Languages:

English, French, Spanish
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