Top-rated for its fully equipped kitchen, perfect for every meal.
Games at the ready
One of the few properties with video games available for guests.
Centrally-located
You're never far from where you need to be with this convenient location.
Discover nearby landmarks
Near Rock Hall Harbor
2 bedrooms1 bathroomSleeps 6
Popular amenities
Swimming pool
Onsite parking available
Pet-friendly
Kitchen
Washing machine
Air-conditioning
Explore the area
Rock Hall, MD
Rock Hall Harbor
Place, Rock Hall Harbor
8 min walk
Ferry Park
Place, Ferry Park
10 min walk
Waterman’s Museum
Place, Waterman’s Museum
13 min walk
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
130 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
2 Single Beds
Sunroom
1 Double Futon
1 bathroom
Bathroom 1
Toilet · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Garden
Dining area
About this property
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Rock Hall - Voted as one of the 10 best towns in Maryland for many years.
There is a Holiday and special event supplemental cost for some designated events.
In "Oysterman Cottage" you can stay the week or two days in a quaint cottage with Chesapeake Bay View of the harbor from 20982 Bayside Avenue in Rock Hall, MD. Rock Hall is known as the Pearl of the Chesapeake an unspoiled waterfront town on the Eastern Shore of the Chesapeake Bay. It has been voted consistently by Maryland Life as the best sunrise and sunset on the bay. It offers magnificent harbors, many fine marinas, over 2,000 boat slips, a broad spectrum of lodging facilities and restaurants, as well as, a host of recreational opportunities. You can walk to Waterman's Crab House, or Harbor Shack restaurant or drive to enjoy Flying Decoy Bar and Grill, Blue Heron Oyster House, JavaRock, Pearl on Main and Osprey Point Inn and Restaurants. Perhaps take an easy drive to Chestertown for the Kitchen at the Imperial Inn. Chestertown has additional downtown shopping.
Kent County and Rock Hall guide use this link: https://www.kentcounty.com/media/tourism/visitors_guide/
Rock Hall 2025 Events (not a complete listing), check local info for specific dates May 10 Garden Club plant sale May 23-25 Chestertown Tea Party May 31-June1 Rock Hall Triathlon June 6-8 Rock Hall Volunteer Fire Company Fishing Tournament July 3-4 July 4th celebration with fireworks on July 3 July 6 Kent County Watermans Day Aug 8-10 Pirates & Wenches Event
September 27-29 Waterman's Triathlon Festival
Rock Hall Fireworks are scheduled each July 3rd. This is a 35-minute show choreographed to patriotic music. It can be viewed from the bay and from anywhere in Rock Hall Harbor.
Rock Hall is a quaint seashore town with a thriving fishing and boating community. The harbor is filled with crab and oyster boats which leave early every morning, returning with heaving baskets of shellfish for the town's fresh seafood restaurants. The main town too is lovely, with two large 18th century mansions on the National Register of Historic Places, three museums which discuss the town's local heritage and the maritime industry, and many picturesque board houses. The town is particularly stunning at sunset, when the warm light envelops the town and harbor in an intense glow.
The Cottage: Our smoke-free cottage has been completely redone, with new furniture, double shower/double sink bath and laundry room. A new back deck was recently. Enjoy our new granite counters and kitchen flooring. It is enjoyed by family and friends and since our move to North Carolina, and has welcomed selected guests.
Two bedrooms (one queen, two twins) and a sleeping porch with pull out queen sofa-bed offers various sleeping arrangements.
New 42" Flat Panel Samsung Smart TV all streaming service with 100+ channels + YouTube with local Baltimore & Washington channels, Netflix + all other streaming services included.
Owner supplies all linens, coffee and laundry items.
We supply Internet and there is also free internet service at the Java Rock Coffee house in the center of town, a great breakfast and lunch stop.
Pet fee is per pet of $150.00 We have pet rules for your review and acceptance.
We will send you our pet policies before billing. Thanks for your understanding.
Keywords: House
Our prices include all fees. No hidden fees.
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Pet rules - My property attracts many pet owners. Pets are considered when fully described in advance. I may restrict the number and type of pets.
Important information
You need to know
Property Registration Number 20982 Bayside Ave, Rock Hall
Property # 53282vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Rock Hall
Located in Rock Hall, this holiday home is in the city centre and on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Sandy Point State Park. The Mainstay and Larrabee Arts Center are also worth visiting. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and cycling nearby.
Does Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD have a pool?
Yes, this property has a pool.
How much does it cost to stay at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD?
As of 26 Aug 2026, prices found for a 1-night stay for 2 adults at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD on 31 Aug 2026 start from £585, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD?
On-site parking is available at the property.
What time is check-in at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD?
Check-in begins at 3:00 PM.
What time is check-out at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD?
Checkout is at 11:00 AM.
Where is Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD located?
Located in the heart of Rock Hall, this holiday home is within a 10-minute walk of Rock Hall Harbor and Chesapeake Bay. Northern Chesapeake Bay and Ferry Park are also within 10 minutes.
About the host
Hosted by James E. Connell
Long time fund raiser with a national consulting practice. We often use the Rock Hall house for an office for our Pennsylvania, Maryland and Delaware clients. All the comforts of home and lots of personal touches.
Why they chose this property
Rock Hall has been a family destination for over 40 years. We have seen it grow but retain the old world charm. More sailboats than people. Consistently voted one of the best areas on the bay.
What makes this property unique
You will enjoy the quite atmosphere and the great views and walks into the sunsets. Full book the local area attractions available. On-site manager should you have any concerns or problems.
Languages:
English
Premier Host
They consistently provide great experiences for their guests