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Family-friendly vacation rentals in Rock Hall

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Rock Hall family-friendly rentals

Family-friendly home rentals with a hot tub

A cozy bedroom features a spacious bed with a quilted coverlet and decorative pillows. A bedside table with a modern lamp sits beside the bed, while a mirrored dresser adds functionality. Soft, neutral tones create a calm environment, enhancing relaxation.
Guest suite in Adelphi
4.84 out of 5 average rating, 208 reviews

Cozy Suite with Hot Tub and Pool

SusannaRating, 5 stars2 months ago
Eric is an amazing host and person! Super friendly when it came to using the amenities and made us feel at home. Has great recommendations for food and local attractions. Beautiful property to walk around or just sit outside! Overall a 10/10 experience while staying at Eric’s home, couldn’t have asked for a better host for our weekend!
Guest favorite
A cozy sitting area features a gray sofa adorned with decorative pillows. A wooden coffee table with a soft faux fur throw sits in front, topped with a saddle, adding a touch of rustic charm to the space. Soft beige carpeting enhances comfort.
Apartment in North East
4.98 out of 5 average rating, 237 reviews

Dusty's House

JuliannaRating, 5 stars1 month ago
Mr. Bill made accommodations when the Airbnb I had originally planned for fell through. He made the transition quick and even made sure my weekend was blocked off at the new Airbnb and not compromising our plans. Forever grateful for the last minute switch
Guest favorite
A serene outdoor area features six Adirondack chairs arranged on a grassy bluff, offering expansive views of the Chesapeake Bay. The water reflects the blue sky dotted with white clouds, while a small sailboat glides across the horizon.
Cabin in North East
4.97 out of 5 average rating, 173 reviews

Waterfront Cabin on the Chesapeake

HannahRating, 5 stars1 week ago
Cannot give enough stars to this property and hosts!!! What’s a paradise on the Bay. The hosts ensured our stay was stress free, comfortable and that we knew all about the location. The property has some of the most comfortable beds we have ever slept on. Linens were high quality and the cabin is spotless! The extra little design features just made it FUN! We spent a lot of time on the deck, in the hot tub, and at the fire pit! The neighborhood is peaceful and the neighbors are so kind and welcoming! Don’t forget to hang out on the dock and definitely walk down to the beach! We will see this property again next year and cannot wait to book it!
Guest favorite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis
4.86 out of 5 average rating, 108 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

ShannonRating, 5 stars3 days ago
This house was absolutely central to all the activities we planned for our trip to Annapolis. Located in a wonderful neighborhood and a beautiful walk away from a tasty coffee shop!
A serene outdoor area features a refreshing swimming pool surrounded by a spacious patio. Metal lounge chairs and tables are arranged neatly, providing comfortable seating. Lush trees and greenery offer privacy, enhancing the inviting atmosphere of the outdoor space.
Home in Davidsonville
4.95 out of 5 average rating, 19 reviews

Annapolis Elegant 5* House -3 Bedrooms Sleeps 6

CharlesRating, 5 stars22 months ago
Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.
Guest favorite
A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.
Home in Severn
4.88 out of 5 average rating, 170 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

SamihahRating, 5 stars2 weeks ago
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!
Guest favorite
A modern kitchen and dining area features rich wooden cabinetry and a dark granite countertop. Stainless steel appliances are present, alongside a dining table with four wooden chairs. A cozy living area with a red couch is visible in the background, illuminated by natural light from a window.
Townhouse in Upper Fells Point
4.95 out of 5 average rating, 689 reviews

Romantic Hot Tub Getaway, Walk to Fells Point

GraysonRating, 5 stars1 week ago
Brandon's place was absolutely perfect! We couldn't have asked for a cleaner or more comfortable space. The location was great and Brandon is an amazing host. We would definitely stay here again!
Top guest favorite
An aerial view captures the expansive waterfront estate surrounded by lush greenery and a tranquil waterway. The pier extends towards the water, while the house is set back from the banks. Nearby structures include docks and quaint homes along the shoreline.
Home in Deale
4.99 out of 5 average rating, 146 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

LauraRating, 5 stars1 week ago
Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!

Family- and pet-friendly home rentals

Superhost
A spacious bedroom features a large bed with a white quilted comforter and dark gray pillows. A wooden bench is positioned along one wall, and a small decorated tree stands nearby, providing soft lighting. The natural light enters through a large window with shades.
Home in Annapolis
4.73 out of 5 average rating, 122 reviews

West Annapolis SuperHost!

TimmyRating, 5 stars5 months ago
Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.
Top guest favorite
A row of charming brick townhouses is presented, each with distinct colors and architectural details. A well-kept front yard features low-maintenance landscaping, with a small table set in the outdoor area. The street is lined with trees, enhancing the neighborhood's appeal.
Apartment in Capitol Hill
4.99 out of 5 average rating, 239 reviews

Capitol Hill-1BR basement apt-Free parking

EmmaRating, 5 stars2 days ago
Incredible place to stay! The hosts were flexible, responsive, and kind. Very accommodating regarding check in and check out. Would highly recommend!
Guest favorite
A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.
Condo in Annapolis
4.94 out of 5 average rating, 398 reviews

Brand New Reno in Historic Dist w 2 Parking spots

MitchRating, 5 stars3 weeks ago
We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.
Guest favorite
The exterior of a charming townhome is showcased, featuring a vibrant front garden with lush greenery and decorative plants. A set of stairs leads up to the entrance, framed by a white railing. The entrance is marked by a blue door, enhancing the inviting look of the property.
Guest suite in Northeast Washington
4.85 out of 5 average rating, 186 reviews

Musical H Street / Trinidad Basement Apt w / parking

HallieRating, 5 stars3 weeks ago
David and Elizabeth’s place was perfect for my fiancé and our dog Kai. We attended a music festival at RFK and it was a short drive away. We actually ended up riding scooters back because it is so close by! There are so many restaraunts and things to do within walking distance. Check-in was super easy and it’s a very homey, comfortable space. The kitchen has a small fridge, toaster oven, microwave and hot plate with pots, pans, and everything you need to prepare a basic meal. We were able to set our dogs crate up (he’s a medium sized husky) perfectly and still had plenty of space to move around. Finding street parking was super easy and close by. You can hear noise from above at times for sure… ear plugs and a night time noise machine are provided to help. Overall we enjoyed our stay!
Superhost
A single-story house features a welcoming entrance with a front door framed by simple step railings. A spacious driveway leads to the home, and a newly fenced backyard is visible to the left, surrounded by well-maintained grass and brick pathways.
Home in Catonsville
4.84 out of 5 average rating, 136 reviews

Delightful 4-Bed Whole House with Easy Parking

NazahRating, 5 stars3 weeks ago
Yangchen’s place was spotless and the perfect location for our drive down to Washington DC this weekend. It was quiet and calm and a great place to relax after a long day of adventuring. My friends and I all got our rest and relaxation in. I would definitely stay again during our trips to DC/Baltimore.
Guest favorite
A panoramic view showcases a cozy two-story house set against a serene waterfront backdrop. Colorful autumn foliage lines the shore, reflecting vibrant hues in the calm water. A grassy area with a small beach adds to the inviting outdoor space, perfect for relaxation.
Home in Perryville
4.93 out of 5 average rating, 218 reviews

Top of the Chesapeake - Private Waterfront Home

DebRating, 5 stars1 month ago
We had a wonderful stay. We enjoyed being outdoors on the deck and walking the shoreline. The interior accommodations were very comfortable and met all our needs and expectations. The weather was perfect, too! Would definitely like to return again. 👍🏻👍🏻👍🏻
Top guest favorite
The exterior of a rowhome is illuminated by warm string lights, casting a soft glow on the brick façade. A vibrant blue door is highlighted, flanked by large windows with wrought iron details. Outdoor seating arrangements are positioned on the front steps.
Townhouse in Patterson Park
4.89 out of 5 average rating, 320 reviews

Parkside Charm & Spaciousness-Family Friendly

StuartRating, 5 stars1 week ago
My wife and I came to Baltimore for a few days to get away and see the sights. The house become an important part of our getaway. First, it was in a very charming neighborhood. Right next to a very nice park. More about this park later. At night the entire tree-lined street lights up making it look magical. The home itself has a certain charm and we felt at home the moment we stepped inside. The house is a short drive away from the Inner Harbor, which was the main attraction of our trip. But we found plenty of other places to visit during our stay. Our final night, back to the park for a leisurely walk to the other side where we found an ice cream shop! What a wonderful way to finish up our trip sitting on a park bench, eating our ice cream, watching the people walk by. Rafi, our host, was fantastic. He responded to all of our questions very quickly and was very friendly. Rafi was the perfect host. Overall we completely enjoyed our stay here. Thank you so much Rafi!
Top guest favorite
A Victorian home displays its charming architecture under a clear blue sky. The front porch, adorned with planters, invites relaxation, while the surrounding landscape features a large tree with delicate branches. The welcoming entrance is framed by a neatly manicured lawn.
Home in Roland Park
4.99 out of 5 average rating, 182 reviews

Charming Victorian home in Roland Park, Baltimore.

NicholasRating, 5 stars1 day ago
Perfect house for our needs! Great, central location with many restaurants within a short walk or drive. In a beautiful residential neighborhood. House is well-maintained & -appointed. Mark was super friendly and responsive leading up to and throughout our stay. Highly recommend - thanks!

Family-friendly home rentals with a pool

Top guest favorite
A large, clear swimming pool is surrounded by a well-maintained patio. A diving board is positioned at the edge, with a brick wall and lush greenery in the background. Sunlight reflects off the water's surface, enhancing the inviting atmosphere.
Home in Chestertown
5 out of 5 average rating, 24 reviews

Chestertown Watson Family Farm

AmyRating, 5 stars2 days ago
Words can’t describe how incredible this home/property is! You have the option to just sit by the water or in the hammock watching the birds play and fish jump, or you can do one of the MANY activities Molly has provided for you. Kayaks, canoes, paddle boards, pickleball, yards games, pool activities, etc are all provided. The family room is all windows so it not only provides the most incredible breeze- it is great for enjoying all the sights even if you’re not outside in it. Inside there are tons of toys for kids- you do not have to bring a thing if you have kids. They have inside toys, outside toys, kids life jackets, goggles, water balloons, rafts, floaties, pack and play…. Molly and her family have thought of it ALL. We are already talking about coming back. Molly was the best host- responsive, helpful and inviting.
Guest favorite
An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.
Cabin in Saint Michaels
4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KateRating, 5 stars2 weeks ago
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.
Superhost
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars1 month ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Top guest favorite
A fenced-in pool area is surrounded by lush greenery, with tall plants and trees creating a natural backdrop. The pool features calm blue waters, and a small paved pathway leads toward it. A black chair is positioned near the entrance of the pool gate.
Guest suite in Catonsville
4.94 out of 5 average rating, 527 reviews

Rollingside: Two-Room Guest Suite

JenRating, 5 stars1 week ago
Calvin's place was exactly what we needed and much more. It was described accurately, yet exceeded expectations with tiny details. For example, there was not only coffee and tea available, but creamer in the fridge, too. We had a peaceful night sleep and a nice shower. I recommend this place to anyone needing a quiet space to work and stay in the area.
Top guest favorite
An outdoor hot tub features a sleek design with built-in jets, illuminated by soft purple lighting. The surrounding area is draped with white curtains, creating a secluded atmosphere. Seasonal use is indicated, adding a touch of relaxation to the outdoor space.
Place to stay in Annapolis
4.94 out of 5 average rating, 121 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

PaulRating, 5 stars1 month ago
We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.
A backyard pool area is depicted with a swimming pool surrounded by green grass. A ladder leads into the water, and a wooden play structure with a slide is visible in the background. The patio features light-colored siding and French doors that open to the exterior.
Apartment in Nottingham
4.87 out of 5 average rating, 135 reviews

Bright and Cozy 2nd floor apt

KrystalRating, 5 stars3 weeks ago
Dorie and her daughter are wonderful hosts. The area is nice and walkable. We took a walk everday while there. Central to shopping and parks. It is a family neighborhood. Dorie initiated contact several times during our trip to see if we needed anything, to clarify check out instructions, and to let us know she was available if needed. This apartment is upstairs, the host lives below. You will enter through your own private entrance. As far as the dust or noise others mentioned...that was not our experience. This isn't a hotel. Theres no housekeeping. The homes aren't brand new. Its a charming apartment with great hosts in a sweet little neighborhood. Think of staying at your aunts place, not the Ritz. If your standards are perfection, you'd likely prefer a hotel. If you are more relaxed and want a ready made apartment that feels more like home than a vacation spot, this is your spot. I found the apartment clean and comfy! Age is not dirt or grime. Just a normal spot! Airbnbs are homes
Top guest favorite
A spacious yard surrounded by lush green fields and trees is visible, with a two-story house and additional structures in the background. The clear blue sky enhances the tranquil farm setting, while the open area indicates ample room for outdoor activities.
Home in Elkton
4.92 out of 5 average rating, 128 reviews

Farmhouse with large in-ground pool and river view

BrianRating, 5 stars2 weeks ago
We were in the area for a lacrosse tournament and hotel living can get old. The Farmhouse was a great break from that and exactly what we were looking for. All the amenities were greatly appreciated.
Top guest favorite
A serene swimming pool is illuminated by soft lighting, surrounded by trees. Lounge chairs are positioned beside the pool, offering a tranquil space for relaxation in the evening ambiance. The mid-century modern guesthouse is partially visible among the foliage, enhancing the secluded atmosphere.
Guesthouse in Highland
4.98 out of 5 average rating, 291 reviews

Woodland Retreat

KatieRating, 5 stars1 day ago
The Woodland retreat is an amazing getaway! My sister and I were extremely happy to spend a weekend at the pool and can't wait to visit again soon!

Quick stats about vacation rentals that are family-friendly in Rock Hall

  • Total rentals

    30 properties

  • Total number of reviews

    1K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

Destinations to explore