Top 10 Airbnb Vacation Rentals In Rock Hall, Maryland - Updated 2024

Celia
Celia 
Updated
| 5 min read

A waterfront town flourishing with timeless charm and beauty, it’s no wonder why Rock Hall is often called the “Pearl of Chesapeake.” The coastline stretches endlessly with beaches and marinas dotting the pretty town on the Eastern Shore of the Chesapeake Bay. Here, it’s easy to get lost in pleasures that feel like remnants of a bygone era, like vintage shops, old-fashioned bed and breakfasts, and happy, friendly locals. As the day winds down, tourists and locals step out for a sunset that will take your breath away every time. For a weekend break or perhaps even longer, renting a home in town is an excellent way to live like a local and gain a better appreciation of the scenic locale. Keep reading to check out our round-up of the top Airbnb vacation rentals in Rock Hall, Maryland.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 07, 2024.

1. Quaint home in an ultra-convenient location (from USD 175)

Nestled under the canopy of a beautiful magnolia tree is a classic home welcoming guests in town. With three bedrooms, five beds, and off-street parking for up to three cars, this vacation rental can accommodate six to eight guests comfortably. Notable perks of staying here are the fireplace, three TVs with Wi-Fi, and roomy living spaces. And with its location within walking distance of local restaurants, cafés, and shops, it’s one of the most convenient places to stay in Rock Hall. The front yard overlooks South Main Street, while the driveway and parking are off Chesapeake Avenue.

Stayed at this property?
Rock Hall, Maryland, United States
19.48 km (12.1 mi) from Sandy Point State Park
111 reviews   Wifi Available
ENTIRE HOME 5 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
good sized kitchen 2 baths washer/dryer
a/c in every bedroom made the night pleasantly cool
Cleanliness:
great place very clean and a great deal
the house is spacious and clean
this home is very clean and cozy and in a great location
that being said it was very clean and had everything that was needed
Host:
john was a wonderful host
john is a great host
john was very helpful
hosts were very helpful and responsive to any issues
also john was very communicative and responsive throughout and great to work with
Location:
nice place and close to town
great location in rock hall on main street close to all the shops and restaurants
amazing location steps from the quaint downtown and the water
great location and easy to get to
great location it’s minutes from eastern neck wildlife refuge and walking distances from the marina
Read more reviews

2. Charming cottage with views of the bay (from USD 299)

Even in a bayside town like Rock Hall, a bay view is a wonderful luxury. If you stay in this vacation rental dubbed “Oysterman Cottage,” you are treated to a stunning sunset every day from the comfort of the front porch. The cottage sleeps up to six people with two bedrooms and a sleeping porch to accommodate everyone. Savor the best catch of the day at fresh seafood restaurants nearby such as the Waterman’s Crab House, which is within walking distance of the rental. Other must-visit spots nearby are the public beach about half a mile (0.8 km) away and the public swimming pool just around 100 yards (91 meters) away.

Stayed at this property?
Rock Hall, Maryland, United States
18.86 km (11.8 mi) from Sandy Point State Park
33 reviews   Wifi Available
Entire cottage 4 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
love the nice soft sheets :) mattresses comfortable
all the rooms were comfortable
Cleanliness:
the house is adorable and incredibly clean
great clean cottage by the bay and excellent seafood places to eat
this is a lovely cottage very clean and comfortable
very clean well-stocked supplies beautiful new bathroom and kitchen excellent location nice floor plan
Host:
james is a great host
host replied very quickly to inquires so flexible with arrangements and check in time
communication with owner was great i would happily stay again
Location:
nice location to bay front and walking distance to local restaurants
the location was great right across the street from the marina and close by to some local restaurants
so nice to be in walking distance to 2 restaurants
awesome location so close to the fun but you can't hear a peep of noise from inside
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3. Idyllic dwelling on a picture-perfect street

Built in the early 1930s, this three-bedroom cottage seamlessly blends classic and modern comforts in a cozy space. There are three spacious bedrooms with four beds that can sleep a total of eight guests. On the front porch, there are two rocking chairs and a love seat for anyone who wants to relax outdoors. With the cottage’s convenient location, you can get to waterfront restaurants, marinas, and the beach on foot.

Stayed at this property?
Rock Hall, Maryland, United States
19.17 km (12.0 mi) from Sandy Point State Park
49 reviews   Superhost Wifi Available
Entire cottage 4 Beds 8 Guests 3 Bedrooms 1 Bathroom

Accommodates: 8

Top guest reviews
Location:
great location a quick easy walk to marinas restaurants and beach
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4. Sunny retreat with delightful outdoor spaces (from USD 245)

Find a home in this lovely three-bedroom cottage with vibrant flowers brightening up the façade. Perks include a gas fireplace in the living room, a fully equipped kitchen, an airy sunroom, and even a delightful potting shed with seating. The bedrooms are cozy with sea-inspired themes that reflect the city’s waterside setting. Additionally, it has air-conditioning and heating to ensure you’ll always be comfortable inside the house. Found a quarter of a mile (0.4 km) from downtown, this pretty hideaway is within walking distance of the best Rock Hall restaurants, shops, and attractions.

Stayed at this property?
Rock Hall, Maryland, United States
19.48 km (12.2 mi) from Sandy Point State Park
102 reviews   Superhost Wifi Available
Entire cottage 5 Beds 6 Guests 3 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
this lovely cottage is comfortable and well appointed
it is warm and cozy with lots of thoughtful and love-filled touches
bob and diane were super responsive kind and even surprised us with fixings for breakfast coffee and snacks
bob and diane make sure you have everything you need to have a comfortable stay
you will not be disappointed such a charmingly cozy space in rock hall
Cleanliness:
the house was clean and well updated
this is a beautiful clean well-maintained cottage in rock hall
the home was clean and very accommodating
the cottage itself was so cute and quaint clean and bright and cheery
house is very clean and in a nice quiet location
Host:
very responsive hosts
bob was a great host answered all our questions and provided great info about the area
the hosts are great and you can tell they really care about their guests
the hosts were responsive and good communicators
great house with super thoughtful hosts
Location:
adorable house perfectly appointed walking distance from everything on main st
there is an amazing park with a play set for kids just a few minutes away
the location is perfect for all and secluded enough for your own privacy
great location hosts very responsive
their house is very cozy and is in a great location in rock hall
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5. Spacious sanctuary with antique touches (from USD 239)

Up to seven guests can share this warm and homey two-bedroom vacation rental in Rock Hall, Maryland. Known as Oyster Cottage, the two-level house features antique doors and hardware that blend well with the modern amenities and equipment in the kitchen and living spaces. The game room with a fold-out sofa gives guests a place for fun and entertainment along with extra bed space for bigger groups. On balmy days, the backyard is a pleasant spot for hangouts. The Oyster Cottage is found along the parade route, making it a great choice for the town’s famous 4th of July celebrations.

Stayed at this property?
Rock Hall, Maryland, United States
19.61 km (12.2 mi) from Sandy Point State Park
66 reviews   Wifi Available
Entire cottage 3 Beds 7 Guests 2 Bedrooms 1 Bathroom

Accommodates: 7

Top guest reviews
Amenities & Room:
the bathroom and kitchen remodels are great and that garden
furniture is a bit dated (but comfortable) but beds could be improved
we loved sitting at the tables in the backyard and cooking meals with friends in the kitchen
the game room is a bonus third bedroom if you need to use it
looks tiny and quaint from the outside but is surprisingly spacious modernized and comfortable on the inside
Cleanliness:
very clean and welcoming
we also appreciated how clean it was
the place was sparkling clean and very comfortable
house was clean and ready upon arrival
very clean and cute we would happily stay again
Host:
host was great
the hosts were very communicative and helpful
very nice accommodations and a very gracious host
fun stay very responsive host
Location:
great location and great accommodations
cute home in a great location
adorable cottage right on main street walking distance to everything
right in the middle of downtown tons of space and just a really great place to relax
perfect location for the annual waterman's triathlon you will love this place owners are wonderful
Read more reviews

6. Recently renovated house for large groups (from USD 350)

Need space for a large group of family or friends? This picture-perfect home on Sharp Street can accommodate up to ten travelers in its four spacious bedrooms. It features classic and clean interiors, including the gleaming kitchen that’s well-equipped with appliances, cooking equipment, and ample counter space. The rooms and bathrooms are all large and decorated in simple elegance, but a definite highlight is the front porch with giant windows overlooking the street, for when you need a breather or some sunshine on your skin. Just a block away from Main Street, it is a standout rental if you want to be near all the main attractions.

Stayed at this property?
Rock Hall, Maryland, United States
19.45 km (12.1 mi) from Sandy Point State Park
30 reviews   Wifi Available
ENTIRE HOME 4 Beds 10 Guests 4 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Cleanliness:
incredibly clean and well maintained
the place was very very clean and well maintained
this was a very spacious clean home
very clean home close to the water with beautiful sunsets
really nice clean and quite place love the location and awesome host
Host:
rick was a great host
rick was highly responsive and helpful
rick is a exceptional host and we are thankful we were able to spend time at his place
Location:
we highly recommend this location
this is a great house in a great location near the water in rock hall
the house was very quaint and was in a great location
great house and host in fantastic location
location was amazing we walked to get coffee and breakfast in the morning
Read more reviews

7. Bayside beach house (from USD 150)

Keep an eye out for the blue house in Rock Hall, which inspires memories of seaside moments of watching the gentle ripples of the water. Known as the Bayside Beach House, the two-bedroom cottage is just steps from the beach. It sleeps four guests, but the house is expansive with plenty of room to relax and unwind. Pristine white interiors and wooden flooring are a crisp combination, appealing to modern travelers who want a laidback home for their coastal vacation. The elevated deck overlooking the backyard offers a peaceful space for morning coffee or evening drinks.

Stayed at this property?
Rock Hall, Maryland, United States
18.45 km (11.5 mi) from Sandy Point State Park
99 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 4 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
we loved the upstairs bedroom sitting/television area and deck - it was very cozy
the cottage itself is very well appointed charming and comfortable
the living area downstairs bedroom bath and kitchen are wonderful
everything is happy serene and comfortable in the cottage
had everything we needed to be comfortable
Cleanliness:
place was as advertised and very clean
very clean quiet well-equipped cottage
the house was sparkling clean
the house is fresh and clean and a very good use of space
the house was sparkling clean when we arrive and that's much appreciated in these covid times
Host:
very friendly people in rock hall and great seafood at the harbor shack
Location:
a nice location for a quiet getaway
it's just a two-minute walk to the beach and super close to the marina
well equipped and in a good location to walk the neighborhood
shipwright cottage is perfectly located in rock hall to ferry park
it is a brief walk to the park and a breathtaking view of the chesapeake bay
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8. Newly renovated cottage by the bay

Another blue cottage by the bay, this four-bedroom bungalow is a peaceful sanctuary for up to eight people. Newly renovated, it offers dreamy Pinterest-like interiors, high-quality furnishings, and individual heating or cooling units in each bedroom for the utmost comfort of guests. Thoughtful touches make every stay a wonderful rental experience, such as complimentary coffee and tea on hand. The screened-in porch at the front of the house provides a sunny space for enjoying meals. Notable attractions nearby include Ferry Park Beach, which is just a five-minute walk away.

Stayed at this property?
Rock Hall, Maryland, United States
18.53 km (11.6 mi) from Sandy Point State Park
47 reviews   Superhost Wifi Available
Entire cottage 5 Beds 8 Guests 4 Bedrooms 1 Bathroom

Accommodates: 8

Top guest reviews
Location:
this is a great house and great location
Read more reviews

9. Attractive rental with plenty of space for families and pets

Tucked in a quiet street in Harbor Woods, this pet-friendly home is a pleasant place to spend a holiday with family and friends. Inside, the space is bright and airy with plush furnishings and plenty of space for up to seven guests. The kitchen is well-equipped with quality appliances and an eat-in counter, as well as a dining table for four. Each of the three bedrooms is spacious, well-lit, and tastefully decorated. Travelers ready to explore can simply walk to the waterside attractions in Rock Hall.

Stayed at this property?

19.4 km (12.1 mi) from Sandy Point State Park
61 reviews   Superhost Wifi Available
Entire residential home 6 Beds 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7

Top guest reviews
Amenities & Room:
the house was clean and the air conditioning was greatly appreciated
everything was in good shape except for the kitchen
Cleanliness:
the house was very clean and well-stocked - jack even left dog bones for the dog
clean and perfect for families
house was clean and check in was easy
jack’s place is exceptionally clean and very easy to access
the house was clean and our sheep dog loved it so much he had trouble calming down
Host:
jack is a wonderful host
jack was an excellent host and came over to introduce himself when we arrived
jack was a great host and was very quick to respond to our messages
most of all jack and lisa were so attentive and responsive
rock hall has a quiet town with very friendly locals
Location:
great location in rock hall
the location was also fantastic
nice place very close to all the action
it was a great location
lots of room great location
Read more reviews

10. Cozy cottage near marinas

The extra-comfy furnishings in this cozy cottage almost makes one tempted to stay in bed the entire day. There are two bedrooms and three beds for up to four guests, along with a fenced-in backyard with a grill and an alfresco area. Enjoy Wi-Fi throughout the property as well as the use of a DVD player and DVDs during laidback nights in the house. The kitchen is excellently equipped with everything necessary to whip up delicious meals, but if you’d rather go out, there are a lot of delicious seafood options available nearby. The beach is also within walking distance of the property.

Stayed at this property?

19.0 km (11.9 mi) from Sandy Point State Park
16 reviews   Wifi Available
Entire residential home 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
bay cottage was comfortable and clean
Cleanliness:
lovely little cottage clean and convenient
clean with all the amenities
Host:
ann was a helpful host prior to our arrival
super friendly people
neighbors were very friendly and rock hall was a nice town for a visit
Location:
great place within close walking distance to everything
great location super cute house and awesome weekend we couldn't ask for more
w in walking distance to so much; even "town" small quiet beach and the nice neighborhood
i recommend for a quiet inexpensive stay in a cute town
Read more reviews

Stunning sunsets and excellent seafood

Whether you want action like kayaking and fishing or a relaxing vacation by the water, Rock Hall is a fantastic choice for a vacation. Begin discovering the charms of the Pearl of Chesapeake in these top Airbnb vacation rentals in Rock Hall, Maryland, which are perfect for your next holiday escape.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Celia Nachura, a freelance writer from the Philippines, consistently seeks fresh encounters, diverse cuisines, thrilling adventures, and compelling narratives in her travels.

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