Family-friendly holiday rentals in Rock Hall

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Popular amenities for Rock Hall family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Guest suite in Adelphi
4.85 out of 5 average rating, 205 reviews

Cozy Suite with Hot Tub and Pool

ShaneRating, 5 stars8 months ago
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.
Guest favourite
Flat in North East
4.98 out of 5 average rating, 234 reviews

Dusty's House

MaryRating, 5 stars1 month ago
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 🐈‍⬛
Guest favourite
Cabin in North East
4.96 out of 5 average rating, 168 reviews

Waterfront Cabin on the Chesapeake

BrianRating, 5 stars1 week ago
This place was amazing! Even cuter than the photos, clean, well-appointed, and the view was everything I needed…even the firepit and fireplace were match-ready!
Superhost
Home in Annapolis
4.87 out of 5 average rating, 175 reviews

Charming Annapolis Water View Home

WalterRating, 5 stars1 month ago
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 couldn’t 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. Can’t wait to check this place out in the summer!
Guest favourite
Villa in Annapolis
4.84 out of 5 average rating, 112 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

MarthaRating, 5 stars6 months ago
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!
Guest favourite
Townhouse in Upper Fells Point
4.95 out of 5 average rating, 660 reviews

Romantic Hot Tub Getaway, Walk to Fells Point

NyasiaRating, 5 stars1 day ago
Brandon was a great host, communicated very nicely and even gave notices regarding the hot tub so we’d 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!
Top guest favourite
Home in Deale
4.99 out of 5 average rating, 139 reviews

Chesapeake Waterfront HotTub-Kayaks-Crabbing

JacobRating, 5 stars2 months ago
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. Can’t wait to go back for the fourth time !
Bungalow in Deale
4.85 out of 5 average rating, 388 reviews

Cozy waterfront getaway on the Bay

MollyRating, 5 stars1 month ago
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

Top guest favourite
Flat in Capitol Hill
4.99 out of 5 average rating, 217 reviews

Capitol Hill-1BR basement apt-Free parking

LukeRating, 5 stars4 days ago
I would have paid more😂 we were upset when we couldn’t book another night due to unavailability
Guest favourite
Guest suite in NoMa
4.9 out of 5 average rating, 119 reviews

Capitol Hill 1BD-Cari's in the City

RebeccaRating, 5 stars3 months ago
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.
Top guest favourite
Townhouse in Patterson Park
4.88 out of 5 average rating, 308 reviews

Parkside Charm & Spaciousness-Family Friendly

SamRating, 5 stars1 week ago
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!
Superhost
Guest house in Glen Burnie
4.81 out of 5 average rating, 170 reviews

Private 1 bedroom house

BeccaRating, 5 stars2 months ago
Always love staying there! Felt right at home and very responsive and respectful host!
Guest favourite
Guest house in Capitol Hill
4.86 out of 5 average rating, 347 reviews

Historic Carriage House + Parking!

KarinRating, 5 stars3 weeks ago
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 can’t be beat. It’s 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!
Guest favourite
Home in Northeast Washington
4.86 out of 5 average rating, 205 reviews

Spacious Beautiful Home with Soul

LoriRating, 5 stars1 month ago
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,
Top guest favourite
Home in Roland Park
4.99 out of 5 average rating, 170 reviews

Charming Victorian home in Roland Park, Baltimore.

MarcieRating, 5 stars2 weeks ago
We have family in Canton and when we visit we consider Marks home our Baltimore home! Six bedrooms…three bathrooms accommodates our large family. The house is 115 years old…we love the preserved history with the modern kitchen and bathrooms. We are so grateful to have found this treasure!
Guest favourite
Flat in Edgewater
4.91 out of 5 average rating, 434 reviews

Pet Friendly Garden Apartment Near Annapolis

AnnMarieRating, 5 stars2 months ago
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

Top guest favourite
Home in Chestertown
5 out of 5 average rating, 22 reviews

Chestertown Watson Family Farm

TaraRating, 5 stars5 months ago
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.
Guest favourite
Home in Wilmington
4.93 out of 5 average rating, 43 reviews

A Home Away From Home

DavidRating, 5 stars4 months ago
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.
Top guest favourite
Guest suite in Catonsville
4.94 out of 5 average rating, 514 reviews

Rollingside: Two-Room Guest Suite

JamesRating, 5 starstoday
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.
Top guest favourite
Home in Cambridge
5 out of 5 average rating, 12 reviews

Turtle's Nest - Hist. Cambridge

ThomasRating, 5 stars3 months ago
We had a wonderful family thanksgiving! The kitchen was perfect for our needs!
Flat in Nottingham
4.87 out of 5 average rating, 125 reviews

Bright and Cozy 2nd floor apt

KatelynRating, 5 stars2 weeks ago
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 you’ve never been. Thanks for a great stay!
Superhost
Home in Arnold
4.91 out of 5 average rating, 99 reviews

Annapolis Sunset Escape

DarrelRating, 5 stars3 months ago
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.)
Top guest favourite
Guest house in Highland
4.98 out of 5 average rating, 282 reviews

Woodland Retreat

DianaRating, 5 stars1 week ago
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.
Superhost
Cottage in Neavitt
4.81 out of 5 average rating, 21 reviews

Grandview Cottage #2 -A special peaceful place!

ClarissaRating, 5 stars5 months ago
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

Destinations to explore

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  2. United States
  3. Maryland
  4. Kent County
  5. Rock Hall
  6. Family-friendly rentals