
Family-friendly holiday rentals in Rock Hall
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Top-rated family-friendly rentals in Rock Hall
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Rock Hall family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Suite with Hot Tub and Pool
Eric was an excellent host. He was very responsive to inquiries from the beginning of our reservations to after the time had lapsed. He was very accessible. The property was as advertised and we very much enjoyed the surprisingly quiet setting with good access to both the town and metro. The rental space was spotless and the grounds were very nice. The hot tub was a nice way to end a day of sight-seeing. Would definitely seek out his accommodations should we be doing anything in the D.C. area in the future.

Dusty's House
Bill and Sandy are so nice and welcoming. I cannot express how thankful I am to them for how they treated our family. My children especially love Cleo đââŹ

Waterfront Cabin on the Chesapeake
This place was amazing! Even cuter than the photos, clean, well-appointed, and the view was everything I neededâŚeven the firepit and fireplace were match-ready!

Charming Annapolis Water View Home
This home is worth it just for the beautiful views of the Chesapeake bay! It was a gorgeous space with plenty of seating for our family vacation. The master bedroom and bathroom were also a highlight for us. The large soaking tub fits two and the shower was amazing. It being winter we couldnât make use of the kayaks but we loved the hot tub and there is a lovely park walking distance from the house. We drove into Annapolis and also spent a day in Baltimore as the house is in a great spot for driving to either. Canât wait to check this place out in the summer!

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*
Our family and friend group of 11 stayed here for three nights. The house was perfect for us and had everything you would possibly need. We loved it so much that we punted some things we were going to do to hang out there. The fire pit on the deck was a fan favorite at night which all of us sat around, talking and laughing. Some people got up early to fish at the pier that we had access to, and my daughter spent time at the beach there. I can't say enough kind words about Paul as a host. He answered all our questions in a timely manner by texting us which not all hosts do. Today, he gave us a later check out time which was helpful in getting so many people up and out! Paul was there when we arrived and was just so gracious. I would highly recommend this place to anyone and would love to come back someday. Thank you so much, Paul!

Romantic Hot Tub Getaway, Walk to Fells Point
Brandon was a great host, communicated very nicely and even gave notices regarding the hot tub so weâd have a nice time enjoying it. The house was clean and everything was accessible, definitely the perfect fit for two or three guests. Would recommend a thousand times over and would book over and over again!

Chesapeake Waterfront HotTub-Kayaks-Crabbing
This home and Natalie are so amazing we had to come back for a third time ! The house as always was clean and beautiful. Enough towels and beds for the entire family. Canât wait to go back for the fourth time !

Cozy waterfront getaway on the Bay
Doug's cottage is just lovely - super clean and airy, comfortable, quiet. In mid-February, the lake must have had 20 swans on it, gliding from one side to the other every morning. It was surreal. We loved nearby Annapolis and the US Naval Academy as well. So much to do, even on a cold and rainy weekend.
Family- and pet-friendly home rentals

Capitol Hill-1BR basement apt-Free parking
I would have paid moređ we were upset when we couldnât book another night due to unavailability

Capitol Hill 1BD-Cari's in the City
I loved my stay at this little flat. It was very clean, and there was a french press and electric tea kettle, which was very nice to have as a person who cherishes my coffee made to order. There were little snacks available, coffee, tea, and sweetners. Cari was very responsive and made sure that I was comfortable, yet was not intrusive at all. I felt safe in the neighborhood and was able to walk downtown to the convention center very easily. It was a quick 10 min bus ride back to the flat. I could park my car next to the flat and walk or ride where ever I needed to go. Even an Uber was only like $15 to get to downtown. There is a lovely little eatery called Laos with very good prices and fast service that is only a quick walk away. I would highly recommend this spot. You will love it and feel very comfortable.

Parkside Charm & Spaciousness-Family Friendly
We really enjoyed our stay! The space was very clean and the neighbourhood was lovely. The hosts were also very easy to communicate with - highly recommend!

Private 1 bedroom house
Always love staying there! Felt right at home and very responsive and respectful host!

Historic Carriage House + Parking!
We were here for a family event, and this location was perfect. If you need a place to stay near the Capitol, this carriage house canât be beat. Itâs close to the tourist sites, but has the quiet neighborhood vibe that I want to experience when I visit places. Wonderful restaurants were a fairly short walk away. The carriage house has a complete kitchen, which would make this a great extended-stay location. The bed was very comfortable, which is important for someone with a bad back. We loved the history of the place too!

Spacious Beautiful Home with Soul
We had a lovely stay at Susan's home. The house is much more spacious than I was expecting and we were more than comfortable as a family of 4 with a dog. The house is spotless and well supplied with kitchen items and linens. The location is perfect - a quiet neighborhood but in walking distance to downtown Takoma Park and a lovely neighborhood park for the kids. Susan was incredibly accommodating when we had to extend our stay unexpectedly,

Charming Victorian home in Roland Park, Baltimore.
We have family in Canton and when we visit we consider Marks home our Baltimore home! Six bedroomsâŚthree bathrooms accommodates our large family. The house is 115 years oldâŚwe love the preserved history with the modern kitchen and bathrooms. We are so grateful to have found this treasure!

Pet Friendly Garden Apartment Near Annapolis
I really loved this AirBnB! It was very dog friendly and was perfect for what we needed! It was clean, super easy to get to, check-in was a breeze. Easily within driving distance of a variety of activities - downtown Annapolis, various parks, etc. Definitely the perfect home-base for some day excursions!
Family-friendly home rentals with a pool

Chestertown Watson Family Farm
We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

A Home Away From Home
One of the best shower heads I have ever had the pleasure to use. Took a ton of will power to not stay in the shower the whole stay. It appears that Ruthie and her family live in the house when guests are not staying. That did not bother me and my guest, but something to note. Really close to a Casino if that is what you are looking for. Less than a 5 min walk.

Rollingside: Two-Room Guest Suite
What an amazing stay! We really enjoyed the comfy bed, the fireplace and the whirlpool bath. The room is furnished with all kinds of wonderful paintings and rocking chairs, a comfy sofa. It was really quite a surprise! Highly recommended.

Turtle's Nest - Hist. Cambridge
We had a wonderful family thanksgiving! The kitchen was perfect for our needs!

Bright and Cozy 2nd floor apt
We enjoyed our stay! It was only for 1 night but it was what we needed after a long day of driving. Dorie was helpful and flexible for our later check in. The proximity to Double Rock Park is perfect! I highly recommend going if youâve never been. Thanks for a great stay!

Annapolis Sunset Escape
My family and I loved this place. It has great views from every room, and while incredibly spacious, it's very cozy. We had space to be private, but still warm places for family experiences. The amenities are great, the kitchen has all you need, and has great dining spaces. Also, Sam and Ilene were very accommodating. They went out of their way to ensure we were online. Finally, I love being near the water and this place delivered. (I want to return in the summer.)

Woodland Retreat
I can't say enough great things about my stay. The interior space is very clean and spacious and the exterior surroundings are so peaceful, quiet, and beautiful, surrounded by nature . The fenced in yard was a treat for my dog who safely enjoyed roaming freely through its landscape as I watched him from the screen porch. Martha and John are great communicators, who made our check in seamless and they catered to us with extra treats like a dog bowl for my dog, delicious red wine, and snacks. There is kitchenette area with a small fridge, Kurig, microwave and some essentials. Similar to what you might find in a hotel room. It was enough for what we needed. There are some great international cuisine Restaurants nearby. My favorite was Mimi's Kabobs & Pizza. The neighborhood has many beautiful horse farms and the area feels safe and friendly. I was visiting for a seminar and it was exactly what I was looking for: dog friendly, private, clean, and safe. I definitely plan to stay again.

Grandview Cottage #2 -A special peaceful place!
Super comfortable beds, super easy to communicate with and very cozy! Right by where we went for a wedding. Overall wonderful!
Quick stats about holiday rentals that are family-friendly in Rock Hall
Total rentals
30 properties
Total number of reviews
990 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
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