10/10 Excellent
Diane W.
22 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
A true gem!
Diane W.
Stayed 4 nights in Jul 2025
Entire home
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.
Reviews
10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6139.4 sq m
Popular amenities
Explore the area
Chestertown, MD
- Washington College16 min drive
- The Mainstay39 min drive
- Rock Hall Harbor40 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)118 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.
Property manager
Robert
Languages
English, French, Spanish
Add dates for prices
Amenities
Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
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Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
- Pool
- Kitchen
- Washer
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10.0 out of 10, (48 reviews)
House Rules
Check in after 2:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs (limit 2 total)
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
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
We should mention
This property does not have any lifts
About the area
Chestertown
Located in Chestertown, this cottage is on the waterfront. The area's natural beauty can be seen at Eastern Neck National Wildlife Refuge and Wilmer Park, while Sumner Hall and Garfield Center for the Arts at the Prince Theater are cultural highlights. Discover the area's water adventures with kayaking and power boating nearby, or enjoy the great outdoors with ecotours and hunting.
Chestertown, MD
What's nearby
- Washington College - 16 min drive - 15.9 km
- Rolphs Wharf Marina - 27 min drive - 23.9 km
- The Mainstay - 39 min drive - 27.0 km
- Rock Hall Harbor - 40 min drive - 27.7 km
- Ferry Park - 42 min drive - 29.1 km
Getting around
Restaurants
- Harbor Shack - 36 min drive
- Waterman's Crab House - 34 min drive
- Java Rock - 33 min drive
- Get The Scoop - 33 min drive
- Fords Seafood - 33 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
10/10 Excellent
Eileen Maroney L.
16 Nov 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best little cottage
Eileen Maroney L.
Stayed 2 nights in Nov 2024
10/10 Excellent
Deborah T.
5 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet Retreat
Deborah T.
Stayed 3 nights in Aug 2024
10/10 Excellent
ann h.
30 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely
ann h.
Stayed 3 nights in Oct 2024
10/10 Excellent
Erin M.
21 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Serene Getaway
Erin M.
Stayed 4 nights in Jul 2024
10/10 Excellent
Deb H.
12 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Deb H.
Stayed 3 nights in Jun 2025
10/10 Excellent
adrian b.
3 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Top quality
adrian b.
Stayed 11 nights in May 2024
About the host
Hosted by Robert
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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