
House holiday rentals in Rock Hall
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Top-rated house rentals in Rock Hall
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Rock Hall house rentals
House rentals with a pool

Chestertown Watson Family Farm
We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!

House in Edgewater Maryland
It was amazing.The pool is so fun.We had bad weather but we were still a little inside.The location is quiet and beautiful. We will come back for sure. Thank you

Bay Breeze Retreat
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

Rockfish Keeper
It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"

The Mariner's House
Wonderful property with lots of amenities!

Large Home with Pool & 7 bedrooms; sleeps 21
This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

The Peaceful Getaway (with private pool & hot tub)
Perfect for a family getaway and retreat. Love how child friendly their home was as well!

*RARE GEM* Pool!Gameroom!*Jacuzzi*Waterfront!
we were looking for something out of the city, private for three businessmen to do some planning for the remainder of the year in beginning of 2025. I found Eli's place exactly as described, sitting out on the edge of the water and Adirondack chair was peaceful and exactly what we needed. It's a short drive in and out of the city so we we were in downtown for a little sightseeing and then made the short trip back to solitude. The house is exactly as described, while we didn't use the game room we did look at it. everything was clean, exactly like the pictures and highly recommended.
Weekly house rentals

Two bedroom small ranch with beautiful forest view
Great location away from city living , beautiful home away from home , & surrounded by total quietness .

Waterfront Paradise w/ Pier - kayak to Chestertown
This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!

Bay Breeze - 3BR Waterfront Chester River Retreat
Katie's house was beautiful. It was very clean, beautifully decorated and in a great location! We look forward to staying here in the future.

Rock Creek Cottage, Waterfront
The place was spotless and had all the amenities we needed for a 4 day stay. We enjoyed the water view and had a crab feast on the deck overlooking the water. It was a perfect Memorial Day weekend.

Waterfront w/ Hot Tub + Dock | Harbor View Haven
Perfect place to relax and celebrate our daughter’s graduation. Would definitely stay there again! Thank you for sharing your home with us!

Bay Home in Annapolis with Private Dock
Beautiful place, beautiful location. Joel thought of anything you could want.

Rock Hall Sharp Street Retreat
We had a great stay in Rock Hall at Rick’s place for our triathlon race weekend. The house was very clean in a quiet neighborhood. It has a fully equipped kitchen and stocked with extra toiletries; which is always helpful. It’s located in a lovely area by the water with great local restaurants and shops. Communication with Rick was excellent and he’s a very responsive and helpful host.

Bayside cottage steps from the harbor
This rental is a total gem! Think of the standard expectation for a good rental, then level up. That's what they did for every detail. They somehow managed to have everything you need to feel comfortable, but had zero clutter. It felt like they really wanted us to have an enjoyable experience. The house is any easy bike ride to Rock Hall's charming downtown and a quick walk to Watermans Crab House, which has many delicious offerings and gorgeous outdoor dining. Rock Hall itself is pretty remote. They have several good restaurants and a decent grocery market, which is more than can be said for most of the other towns in this area. If you're looking to be off the beaten path, you'll love it here.
Private house rentals

Waterfront Paradise on Seneca Creek w/Hot Tub
Nicki was an exceptional host—responsive, thoughtful, and truly dedicated to providing a wonderful experience. The home was absolutely stunning, equipped with everything we needed, and her attention to detail was impressive. She truly thought of everything, making our family trip seamless and memorable. The property was in pristine condition—immaculately clean, set in a peaceful and quiet location with breathtaking views. I honestly can't say enough great things about this home! As a Realtor, I will be recommending it to all my clients, family, and friends. We can't wait to rebook our stay there again soon!

Spacious4BR home with waterviews
5 adults, 2 children under age 6 stayed at Courtney's home, which was just as described and pictured on the airbnb web page. Great location for our stay for wedding weekend; very comfortable furniture (sofas, chairs, beds; many amenities provided for guests; terrific well-stocked kitchen; very large screened-in porch w/ nice view of Chesapeake Bay and surroundings; spacious bedrooms; 4 full bathrooms; very clean when we arrived. I could go on .... Courtney is a very good communicator, and responded quickly to the few questions we really had. She is a great host and the house was terrific for our needs.

*Waterfront Sunset Bayview* sleeps 6
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

Waterfront Farmhouse Meets Modern Luxury
The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

Lovely Home in Chestertown With Free EV Charging
Perfect place for our during a nearby wedding. Teddi was always responsive, pleasant, and helpful.

Kent Island Escape
The place is absolutely gorgeous. Unfortunately, even though it is waterfront there isn't a good way to access the water for swimming or kayaking due to the way the breakwall is structured.

Stunning Chesapeake waterfront home
We had a truly wonderful stay at this beautiful home! The place was spotless and very well maintained, and we felt comfortable from the moment we arrived. There were plenty of activities to enjoy as a family, and we created some unforgettable memories here. The host was incredibly friendly and responded quickly to any questions we had, which made everything even more enjoyable. The surroundings are absolutely stunning, and the sunset views were nothing short of magical. We would love to come back again!

Kent Island Waterfront Home
We really loved our stay! The house feels super cozy and has a lot of nice modern touches. The LED lighting throughout gives it a really relaxing vibe, and the big smart TVs were awesome for movie nights. The kitchen had everything we needed, and we appreciated the quality cookware and silverware. There were USB ports everywhere which was super convenient. But honestly, the best part was waking up and seeing the lake view for the first time—we arrived at night and were totally blown away when we saw it in the morning with a cup of coffee. The walkways and dock were great for enjoying the outdoors, and overall the whole place just felt peaceful and well thought-out. The hosts were really kind and attentive, and it showed. If you’re able to, we’d definitely recommend booking an extra day just to relax and enjoy the house—we were in town for a wedding and didn’t get as much time there as we would’ve liked. We’d love to come back!
Quick stats about house rentals in Rock Hall
Total rentals
20 properties
Total number of reviews
680 reviews
Family-friendly rentals
20 properties are a good fit for families
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Waterman's Crab House, Harbor Shack and Osprey Point Inn
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Hampden
- District Wharf
- Smithsonian National Museum of Natural History
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Quiet Waters Park
- Crystal Beach Manor, Earleville, MD
- Caves Valley Golf Club