
Kid-friendly holiday rentals in Assateague Island
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Top-rated kid-friendly rentals in Assateague Island
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Child-friendly house rentals

Private pool, waterfront, kayaks, bikes, firepits!
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!

Charming Waterfront Cottage w/2 King Suites + Dock
We were blown away by how amazing the house was. We came for a weekend event in OCMD and found ourselves not wanting to leave the house. The backyard and dock leading to the water were relaxing and created a lot of great photos and memories for us. Being able to wake up and go kayaking before starting the day followed by sitting around the fire at night really made for a perfect stay.

Joy in the Morning @ Berlin Boho Bungalow
Beautifully decorated, great location and Kristen was responsive when needed…a real gem of a home.

SpaciousCondo nearOcean City|Winery|Golf on 5Acres
This was a great place to get away for some peace and quiet. We had a lacrosse tournament in Berlin and the field was 15 minutes away. Beautiful home and very cozy. Very easy check in and Brenda was very quick to answer any question. Totally worth it!

Wagon Wheel Cottage
I loved it, since I arrived, the environment was very quiet and private, the house was very clean and organized, we had a great time, I will definitely return

Central Location- Walk to Dining & Entertainment!
I highly recommend this place!! The house was newly remodeled, very clean, had nice decor and furnishings and most of all felt like home. The hosts were wonderful to deal with and very accommodating!! Thanks for a wonderful place to stay during our family vacation ❤️

Pearl in the Pines
Had a great time in this lovely home! We especially enjoyed the large screen porch and being able to walk to the boat dock for some kayaking.

Bayshore Beach Bungalow 46 w/ Boat Slip!
My family has a wonderful stay at this Airbnb. the hosts were accommodating in that we needed an extended stay and were very responsive. The location is nice, it's walkable to the beach. Also with a short walk you can see the sunrise or sunset. Waterfront access is nice although we didn't utilize it. The unit looks as advertised. It was cozy for our stay. The couch was comfortable. The hosts have gone out of their way to provide utensils and other kitchen items that were very useful for our time there. We are very grateful for our time there and would recommend it highly.
Kid-Friendly apartment rentals

Downtown Main Street Berlin Apartment
Excellent location and host. Sonny had water, coffee, beer, and snacks in the apartment for us. Also, pamphlets and town map of things to do. Very clean and comfortable. Would recommend.

Amazing oceanfront view 3 blocks from boardwalk
Condo was exactly as described! Amazing oceanfront view! I was also impressed with how much room there was. It was cruiser week so it was a tad bit noisy at night, but other than that and the fact we couldn’t stay longer, we had a wonderful time and enjoyed our stay!

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+
Had an amazing time at this beautiful beachfront Airbnb. The location couldn’t have been better, literally steps from the sand with stunning ocean views right from the balcony. The space was clean, cozy, and had everything we needed for a relaxing getaway. The host was friendly, responsive, and made check-in a breeze. Highly recommend this spot for anyone looking to unwind by the water.

The Artist’s Barn Studio
This place is lovely! It is a little bit of a walk to the beach, but it's a perfect distance to most of the boardwalk area. The place is well-maintained and thoughtfully furnished. I would stay here again.

DeweyBeach 1 BR + sleeper sofa. Walk to the beach!
Great spot; host was extremely responsive and clearly took the time and care to ensure we had a frictionless experience. Thank you Ben!

Farm View Suite
Donna & Neal’s “sweet suite” was absolutely PERFECT! Beautifully decorated to every detail to make you feel relaxed, cozy & at home! Donna was great at communicating check-in details & any other info or suggestions we may need. We were able to meet Donna & Neal, they are the most kind & sweet people! The suite was VERY clean & free of any chemical cleaner smell like another review mentioned & I really appreciated that. We loved all the treats, fresh flowers & special touches just for us & to feel so welcomed in their lovely town of Frankford. The bed was super comfy, kitchen area had everything you would need, bathroom & shower was AMAZING! This was a last minute getaway for us so we feel so fortunate to have found such a beautiful place to stay! The only Airbnb in the area that met all our needs & wants! We will 100% return again & recommending the “sweetest suite” to all our family & friends! Truly believe this trip was meant to be & our paths were meant to cross w/Donna & Neal!

Newly renovated cute apartment 🏄 12 street 🌸
I did a quick overnight stay with my husband and toddler, the place suited just that plus some. We comfortably could’ve stayed longer and would consider it again in the future. The bedroom was large and the living room was plenty spacious for my toddler to play. The location was walkable and not too busy even for Memorial Day weekend. Mihaela was a great host and very responsive!

Pansy’s Retreat
I had such a wonderful experience at this Airbnb! From the moment I walked in, I could tell how much care and attention went into the space. It was spotlessly clean, with everything neatly arranged and thoughtfully stocked. The homey touches made it feel warm and inviting. The neighborhood was incredibly peaceful and quiet. I wouldn’t hesitate to book again. Highly recommend to anyone looking for a clean, cozy, and tranquil place to unwind!
Child-Friendly Holiday Condos

Family Condo Oceanside in Midtown OC
Brian and his family were amazing. As soon as we booked they were very accommodating. This continued into the stay and it was so lovely to stay somewhere with the kids in mind.

Stylish Apartment Steps From the Beach
I had a lovely stay! The house was so chic, cute, and most importantly CLEAN! Loved being steps away from the beach! I had a wonderful little solo getaway, where I could get work done and relax right afterwards! I will definitely be back! 😊

Bayside Retreat in the Heart of Ocean City!
We loved staying at Heathers place. Very comfortable and felt like home. We really appreciated the Welcome book she provided which gave us all kinds of recommendations for food, drink and activity. We will be coming back!

Direct Oceanfront close to Northside Park!
Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!

Getaway in Ocean Pines
Selena was a wonderful host. She had everything that one can think of when staying at a 5 star hotel! Coffee, sugar and creamer, soaps and creams, extra blankets, cookware and crockpots and big beautiful towels. Her place was so comfortable and clean and neat. I will absolutely recommend this place to my friends and family back home. The beach passes are really also so great because one doesn’t have to search the streets to find parking. The Yacht Club has nice live music and it was a great stay!!! Thank you Selena.

Direct Oceanfront with a View and Amenities Galore
Bryan is super responsive and easy to communicate with. He notified us of detailed check in and check out instructions. He then checked in on us towards the end of the trip to make sure all of our expectations were met; to which they were. This condo is exactly as described in the listing and pictures. It’s clean and cozy. The view from the bedroom is unmatched. The location is perfect in a sense that it’s not too close to the boardwalk, making the area a little more quiet, but also within 10 mins to the best restaurants and bars. The staff at the condo and even other guests were friendly and courteous. If you’re afraid of heights, this might not be the best place to stay for you, but as I previously mentioned, the view from the master bedroom can’t be beat. That view alone, would have us stay again. I would definitely recommend this stay to others.

Caramar Couples Retreat
There aren't enough words proper enough to describe how spot on this amazing place is. It looks EXACTLY as the photos show. As soon as I walked in the door, I was met with a beautiful & relaxing relief. I literally let out an "Oh my gosh". I just knew, it was going to be enjoyable. It was quiet & so serene. The bed truly is so comfortable. I was also so impressed with the amount of kitchen supplies as well as the products that were offered in the bathroom & kitchen. They were not your typical "hotel brand" products. Plenty of nearby places within walking distance from food to shopping. I hope I was a good a guest for them because I want to return again. I am in love with it. Such an amazing getaway. Thank you ×100!

Luxury Oceanfront Escape!
We had an amazing stay! The place was clean, the bed was very comfortable and the view off the balcony was amazing! Shiri was incredibly responsive and kind. Would definitely recommend this place!
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