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.
Top guest reviews
Amenities & Room:
good sized kitchen 2 baths washer/dryera/c in every bedroom made the night pleasantly coolCleanliness:
great place very clean and a great dealthe house is spacious and cleanthis home is very clean and cozy and in a great locationthat being said it was very clean and had everything that was neededHost:
john was a wonderful hostjohn is a great hostjohn was very helpfulhosts were very helpful and responsive to any issuesalso john was very communicative and responsive throughout and great to work withRead more reviewsLocation:
nice place and close to towngreat location in rock hall on main street close to all the shops and restaurantsamazing location steps from the quaint downtown and the watergreat location and easy to get togreat location it’s minutes from eastern neck wildlife refuge and walking distances from the marina
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.
Top guest reviews
Amenities & Room:
love the nice soft sheets :) mattresses comfortableall the rooms were comfortableCleanliness:
the house is adorable and incredibly cleangreat clean cottage by the bay and excellent seafood places to eatthis is a lovely cottage very clean and comfortablevery clean well-stocked supplies beautiful new bathroom and kitchen excellent location nice floor planHost:
james is a great hosthost replied very quickly to inquires so flexible with arrangements and check in timecommunication with owner was great i would happily stay againRead more reviewsLocation:
nice location to bay front and walking distance to local restaurantsthe location was great right across the street from the marina and close by to some local restaurantsso nice to be in walking distance to 2 restaurantsawesome location so close to the fun but you can't hear a peep of noise from inside
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.
Rock Hall, Maryland, United States
19.17 km (12.0 mi) from Sandy Point State ParkSuperhostAccommodates: 8
Top guest reviews
Read more reviewsLocation:
great location a quick easy walk to marinas restaurants and beach
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.
Top guest reviews
Amenities & Room:
this lovely cottage is comfortable and well appointedit is warm and cozy with lots of thoughtful and love-filled touchesbob and diane were super responsive kind and even surprised us with fixings for breakfast coffee and snacksbob and diane make sure you have everything you need to have a comfortable stayyou will not be disappointed such a charmingly cozy space in rock hallCleanliness:
the house was clean and well updatedthis is a beautiful clean well-maintained cottage in rock hallthe home was clean and very accommodatingthe cottage itself was so cute and quaint clean and bright and cheeryhouse is very clean and in a nice quiet locationHost:
very responsive hostsbob was a great host answered all our questions and provided great info about the areathe hosts are great and you can tell they really care about their gueststhe hosts were responsive and good communicatorsgreat house with super thoughtful hostsRead more reviewsLocation:
adorable house perfectly appointed walking distance from everything on main stthere is an amazing park with a play set for kids just a few minutes awaythe location is perfect for all and secluded enough for your own privacygreat location hosts very responsivetheir house is very cozy and is in a great location in rock hall
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.
Top guest reviews
Amenities & Room:
the bathroom and kitchen remodels are great and that gardenfurniture is a bit dated (but comfortable) but beds could be improvedwe loved sitting at the tables in the backyard and cooking meals with friends in the kitchenthe game room is a bonus third bedroom if you need to use itlooks tiny and quaint from the outside but is surprisingly spacious modernized and comfortable on the insideCleanliness:
very clean and welcomingwe also appreciated how clean it wasthe place was sparkling clean and very comfortablehouse was clean and ready upon arrivalvery clean and cute we would happily stay againHost:
host was greatthe hosts were very communicative and helpfulvery nice accommodations and a very gracious hostfun stay very responsive hostRead more reviewsLocation:
great location and great accommodationscute home in a great locationadorable cottage right on main street walking distance to everythingright in the middle of downtown tons of space and just a really great place to relaxperfect location for the annual waterman's triathlon you will love this place owners are wonderful
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.
Top guest reviews
Cleanliness:
incredibly clean and well maintainedthe place was very very clean and well maintainedthis was a very spacious clean homevery clean home close to the water with beautiful sunsetsreally nice clean and quite place love the location and awesome hostHost:
rick was a great hostrick was highly responsive and helpfulrick is a exceptional host and we are thankful we were able to spend time at his placeRead more reviewsLocation:
we highly recommend this locationthis is a great house in a great location near the water in rock hallthe house was very quaint and was in a great locationgreat house and host in fantastic locationlocation was amazing we walked to get coffee and breakfast in the morning
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.
Top guest reviews
Amenities & Room:
we loved the upstairs bedroom sitting/television area and deck - it was very cozythe cottage itself is very well appointed charming and comfortablethe living area downstairs bedroom bath and kitchen are wonderfuleverything is happy serene and comfortable in the cottagehad everything we needed to be comfortableCleanliness:
place was as advertised and very cleanvery clean quiet well-equipped cottagethe house was sparkling cleanthe house is fresh and clean and a very good use of spacethe house was sparkling clean when we arrive and that's much appreciated in these covid timesHost:
very friendly people in rock hall and great seafood at the harbor shackRead more reviewsLocation:
a nice location for a quiet getawayit's just a two-minute walk to the beach and super close to the marinawell equipped and in a good location to walk the neighborhoodshipwright cottage is perfectly located in rock hall to ferry parkit is a brief walk to the park and a breathtaking view of the chesapeake bay
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.
Rock Hall, Maryland, United States
18.53 km (11.6 mi) from Sandy Point State ParkSuperhostAccommodates: 8
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.
19.4 km (12.1 mi) from Sandy Point State ParkSuperhostAccommodates: 7
Top guest reviews
Amenities & Room:
the house was clean and the air conditioning was greatly appreciatedeverything was in good shape except for the kitchenCleanliness:
the house was very clean and well-stocked - jack even left dog bones for the dogclean and perfect for familieshouse was clean and check in was easyjack’s place is exceptionally clean and very easy to accessthe house was clean and our sheep dog loved it so much he had trouble calming downHost:
jack is a wonderful hostjack was an excellent host and came over to introduce himself when we arrivedjack was a great host and was very quick to respond to our messagesmost of all jack and lisa were so attentive and responsiverock hall has a quiet town with very friendly localsRead more reviewsLocation:
great location in rock hallthe location was also fantasticnice place very close to all the actionit was a great locationlots of room great location
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.
19.0 km (11.9 mi) from Sandy Point State ParkAccommodates: 4
Top guest reviews
Amenities & Room:
bay cottage was comfortable and cleanHost:
ann was a helpful host prior to our arrivalsuper friendly peopleneighbors were very friendly and rock hall was a nice town for a visitRead more reviewsLocation:
great place within close walking distance to everythinggreat location super cute house and awesome weekend we couldn't ask for morew in walking distance to so much; even "town" small quiet beach and the nice neighborhoodi recommend for a quiet inexpensive stay in a cute town
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.
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