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Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

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20982 Bayside Ave, across from town dock, close to harbor and restaurants
Living room connected to MB and kitchen
Living room view 3
Living Room View 4
New kitchen counters and floor view 2

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 61000 sq ft

Popular amenities

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

Explore the area

View in a map
Rock Hall, MD
  • Place, Rock Hall Harbor
    ‪6 min walk‬
  • Place, Ferry Park
    ‪10 min walk‬
  • Place, The Mainstay
    ‪17 min walk‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪110 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.

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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
With prior approval pet fee and pet deposit
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Smoking

Smoking is not permitted
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

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
Property Registration Number 20982 Bayside Ave, Rock Hall

We should mention

A car is required for transport to and from this property

About the area

Rock Hall

Located in Rock Hall, this holiday home is in the city centre and on the waterfront. Rock Hall Harbor and Rolphs Wharf Marina are worth checking out if an activity is on the agenda, while those looking for area attractions can visit The Mainstay and Larrabee Arts Center. Garfield Center for the Arts at the Prince Theater and Paul Reed Smith Guitars 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 hiking and hunting nearby.
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Map
Rock Hall, MD

What's nearby

  • Rock Hall Harbor - 6 min walk - 0.6 km
  • Ferry Park - 10 min walk - 0.9 km
  • Waterman’s Museum - 13 min walk - 1.1 km
  • The Mainstay - 17 min walk - 1.5 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 127 min drive

Restaurants

  • ‪Tolchester Marina Beach Bar - ‬13 min drive
  • ‪Ford's Seafood - ‬3 min drive
  • ‪Harbor Shack - ‬4 min walk
  • ‪Chester River Seafood - ‬8 min drive
  • ‪Waterman's Crab House - ‬7 min walk

Frequently asked questions

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 Mar, 2026, prices found for a 1-night stay for 2 adults at Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD on 30 Mar, 2026 start from S$332, 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, Chesapeake Bay and Northern Chesapeake Bay. Ferry Park and Waterman’s Museum are also within 15 minutes.

Reviews

9.8

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. 58 out of 66 reviews
Rating 8 - Good. 7 out of 66 reviews
Rating 6 - Okay. 1 out of 66 reviews
Rating 4 - Poor. 0 out of 66 reviews
Rating 2 - Terrible. 0 out of 66 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

David G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We have always enjoyed our stays here.
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Brian W.

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

H

Great place to stay
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Jan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My husband and I enjoyed a relaxing week in Rock Hall.Very comfortable place to hang out when not at the beach or walking around town.Clean place and well equipped kitchen.
Stayed 4 nights in Sep 2025
Verified

10/10 Excellent

David M.

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

wonderful!

Had such a great time at this cottage...would definately come back! Close to downtown activities and easy walking to water. Enjoyed our time there!
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Barbara F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We are repeat visitors and have always enjoyed staying at Oysterman Cottage. The cottage is clean, the kitchen is well-stocked, the beds are comfortable, the shower is amazing! The screened in porch is a great place to relax or eat meals. The location is great, close to our favorite restaurants. We look forward to our next visit!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Tressa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Oysterman Cottage was absolutely delightful, just perfect for my elderly parents because both bedrooms were on the first floor, and very comfortable! Plenty of linens and extra towels, fully stocked coffee bar, and the owner was extremely responsive and very friendly. It was our first time in Rock Hall, and we found everyone in the quiet cozy community friendly and very helpful. We will definitely be back!!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

David G.

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

Nice place

It’s a nice place
Stayed 10 nights in Jul 2022
Verified

10/10 Excellent

Kerry B.

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

Great Location!

Property was exactly like listed. Location was perfect for us and we had a fantastic time in Rock Hall visiting with family!
Stayed 2 nights in Aug 2019
Verified

10/10 Excellent

Barbara F.

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

Lovely Cottage

We love staying at this cottage! The kitchen is well stocked, the screened-in porch is wonderful. Within walking distance of our favorite restaurants. We had a great weekend and look forward to our next visit!
Stayed 3 nights in Sep 2023
Verified

8/10 Good

Nancy N.

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

Great place near the water

Great place near the marina. Kitchen was well equipped for cooking our own meals. Nice recent updates to the bathroom and kitchen. Covered porch out back is also quite nice. We enjoyed our stay and would gladly return to this house!
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Nicole R.

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

Absolutely amazing in every way! Location, beach, restaurants, town!

My three week stay with my boys and I was absolutely amazing. The house was great, stocked with everything needed, perfect size, perfect location, great communication w owner and property management- phenomenal customer service from everyone! Just a secret gem- I can’t speak more highly enough about this VRBO and its owners!
Stayed 16 nights in Jul 2023
Verified

6/10 Okay

Carol D.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Perfect accommodations for Waterman's Triathlon

Cottage had everything we needed although kitchen applicances could use some updating.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Sharon S.

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

Wonderful cottage in Rock Hall, Maryland!!

I really enjoyed the accommodations at the Oysterman Cottage!! The cottage was immaculate and completely decorated in a nautical theme which is so appropriate since Rock Hall is a small fishing town!! Also, loved the screened porch for reading and enjoying breakfast and dinner!! Thanks again for a wonderful stay in Rock Hall!!
Stayed 4 nights in Jul 2022
Verified

10/10 Excellent

Kelly K.

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

Super clean and well equipped

This was probably the cleanest rental I’ve ever stayed in. Everything that you could possibly need was there. Location was great, with bay views and walking distance to restaurants and the beach. Would definitely recommend this house!
Stayed 2 nights in Jul 2020
Verified

10/10 Excellent

David G.

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

Happy Birthday Week

Very well kept cottage. Its location is ideal for walking to restaurants on the water. We enjoyed the back porch with birds singing and shade from the large oak trees. A large bath was a nice feature/
Stayed 10 nights in Jul 2021
Verified

10/10 Excellent

Julie F.

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

Authentic Rock Hall Beach Cottage In Great Location!

This charming cottage is located in a very convenient spot. Walking distance to the beach, pool, restaurants and Main Street for shopping. The interior had plenty of space for our family of four & our lab. Well stocked kitchen and bath with a grill out back. Our kids are looking forward to a return!
Stayed 7 nights in Sep 2020
Verified

10/10 Excellent

Andrew W.

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

Excellent Cottage and Location

The cottage is a very comfortable spot for a relaxing few days in Rock Hall It is ideally situated near town, the harbor, and restaurants. Diane was very easy to reach for questions and tech support. The kitchen is well equipped. We will rent this cottage again. Thank you for making it available AW
Stayed 5 nights in Jun 2022
Archival

10/10 Excellent

Jeanne T.

A comfortable, relaxing weekend!

This property was one of the best equipped that we have ever rented; anything we might have needed was included in the kitchen inventory. Beds were very comfortable and linens very adequate. The living room and also the sunporch provide lots of seating. Rock Hall is a charming town for walking around. The only drawback is that the bathroom is off one of the bedrooms, but not a big problem when it's family.
Verified

10/10 Excellent

Charlotte G.

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

Wonderful cottage and location

This is my second year staying at the house. I go every year to Rock hall MD for a ladies fishing trip. The house is spacious and really has everything we need to stay comfortably. We do wish there was another bathroom or half bath but the bathroom that they have is very large and easy enough to double up while getting washed up or makeup and hair. We spent a lot of time on the back screened in porch. We also love the location because we can walk to the restaurants and the town pool and harbor.
Stayed 2 nights in Jul 2023
Verified

10/10 Excellent

Charlotte G.

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

Always a great stay

My friends and I stay here every year because it’s so convenient to the harbor, restaurants and a walk or shuttle to the town. The shuttle service was new this year since it shut down in 2020. I am happy this is back again! The house is always well stocked with items we need. I’d recommend bringing an extra roll of paper towels as we go through quite a bit. There are 6 ladies who stay in this house and we always manage with one bathroom! The back screened in porch is wonderful.
Stayed 2 nights in Jun 2024
Verified

8/10 Good

Beverly Z.

Oyster man cottage

Clean and well set up. Good seating in the living room. Well stocked kitchen. No bowls for cereal or ice cream. Only one bathroom and in the bedroom. The book with cottage information should be updated. We enjoyed our stay very much.
Stayed 2 nights in Oct 2018
Verified

10/10 Excellent

Sandi R.

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

Perfect escape

Wonderfully situated cottage. Just a few yards from marina and about 10-15 minute walk to small beach and 30 minute drive to a larger beach. A few great restaurants within walking distance, including great seafood (Ford’s, Waterman’s, Harbor Shack), pizza (Anchor and Plow) and ice cream. Small grocery store and local food market so didn’t have to drive much. Amazing birdwatching, hikes and kayaking. A terrific place to get away and unplug. The house was very clean and well-stocked. Very nice closed in porch for bug-free outdoor dining.
Stayed 14 nights in Aug 2021
Verified

10/10 Excellent

Judy R.

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

Lovely, Peaceful Stay in Rock Hall

This is our 2nd time staying at this cottage. Each time the home was clean and well stocked and did have start-up supplies for guests. It is conveniently located and within walking distance to marina, restaurants, bay, etc. We enjoyed sitting and eating on the peaceful, screened-in back porch that overlooks a large tree shaded backyard. The host was also accommodating with a special request we had. It is also a plus that it is pet friendly and there was no evidence that any pets had been there prior to our arrival. So, if you have a pet or not, this is a lovely place to stay. Since we have family in the area, we will continue to stay here during our family visits.
Stayed 2 nights in May 2022
Verified

10/10 Excellent

Verified traveller

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

Great Escape from DC

We wanted a change of scene for Thanksgiving this year and this cottage was perfect. The three of us cooked together in the large, well-equipped kitchen and enjoyed reading and watching movies in the comfortable living room. We all slept well and appreciated the spacious, new bathroom. At the end of the day, we were treated to the most spectacular sunsets imaginable, only a short walk from the cottage. Although the weather was unusually warm for Thanksgiving, I wished it were warmer so we could've spent more time on the large screen porch. It's a sweet cottage and I've recommended to a friend already!
Stayed 2 nights in Nov 2022
Verified

8/10 Good

WAYNE W.

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

No A.C.

Besides No air-conditioning and it was 90 kind of wrecked it but Everything else was perfect. Location was perfect When we checked in the a.c. wasn't working. I contacted management and they sent someone right out. He needed to order a part. We like it there. We want to come there next year for pirates weekend
Stayed 2 nights in Aug 2023

About the host

Hosted by James E. Connell

Host profile image
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
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