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 July 27, 2024.
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1. Quaint home in an ultra-convenient location (from USD 159)
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.
2. Charming cottage with views of the bay (from USD 290)
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.
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 ParkSuperhost
Accommodates: 8
4. Sunny retreat with delightful outdoor spaces (from USD 275)
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.
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.
6. Recently renovated house for large groups (from USD 237)
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.
7. Bayside beach house (from USD 250)
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.
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 ParkAccommodates: 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 ParkAccommodates: 7
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
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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