Waterfront holiday rentals in Assateague Island

This unit was everything we wanted for a Memorial Day Weekend stay. It was steps from the beach. Extremely clean which is important to us as a family with kids. Would like to stay here again in the future. A+ Hosts

Mike’s place was perfect for our stay. Close to the bus stop and within walking distance to everything we needed. It was perfect for our weekend away!

A beautifully decorated and spacious condo with a gorgeous view. Great location to beach and boardwalk. Lots of little detailed amenities to make our stay comfortable.

Hand down what an AIRBNB is supposed to be. The place is just like the pictures and smells crystal clean upon arrival. The mattress and linens were so comfortable it had me wanting to replace my mattress! This was the perfect place for annual girls weekend. Let me explain how gracious they were. We had previously picked a different Airbnb and the moment we walked into the place realized we had been PUNKED. I wont get into that whole story but needless to say it was nothing like what was advertised and we actually felt unsafe. I reach out to Steven immediately and he responded right away. Although the reservation would mean us checking in within hours of the booking he was willing to accommodate us with very short notice. The communication was flawless and Steven was truly our saving grace for the trip. What turned into a rough start ended on a very high note. Thank you, again Steven!

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!

Laura was a very responsive and wonderful host! She went above and beyond with providing a variety of things to do and see during our stay. She also made sure the check in and check out process went smoothly. The home was well kept, clean and had a great view! Being able to relax on the back porch with the sound of the waves was so peaceful. Our family had a great stay and will definitely be back! Thank you Laura!

I was so impressed with Kara’s condo. It was everything I hoped it would be. The decor is very nice and the kitchen is wonderful— modern, spacious, and containing anything you need for cooking or entertaining. The view of the ocean from the 19th floor is both spectacular and calming, whether on the spacious balcony or looking down through the bedroom’s floor to ceiling windows. The building is great. Everyone was friendly and this is a very nice part of Ocean City. Lastly, Kara was terrific. Kind and a great communicator. Plus check in was smooth. If you’re considering a two bedroom, two bathroom condo in this area, I highly recommend this listing!

We arrived the Saturday of Memorial Day Weekend 2025. The directions were specific and spot on. Great parking and easy access. This host went above and beyond to accommodate their guests. Fabulous location! Clean, immaculate and extremely inviting. Balcony was large and truly made you feel like you were on vacation with all the beachy whimsical decor, not too much, just enough! Everything very tastefully equipped. We will be back! Easy access to the beach and the pool, yet private. Thank you. (Crab Stop is the ONLY spot to get your crabs etc, absolutely amazing people!)

We love our stay here! The house had everything we needed and more. It was easy to find, and the views were amazing. We spent the whole time outside in the nature, and we loved how quiet it was. Kevin was easy to reach for any questions we had, and we appreciated his help. We would definitely come back here in the future.

Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!

Great spot for a mother/daughters retreat. We enjoyed the cozy and cute decor and each having our own space in the Seaside Cottage. Also, the kitchen was will equipped and we made several meals together as a family. Just a short drive to everything on the island and super close to water and the Misty Pasture. Kathleen was a wonderful host— responsive and proactive throughout our stay. We had a wonderful visit!

My family and I had a wonderful stay at Bobs!! We will be back! Quiet and peaceful but close to all the attractions too, just a short 20 min drive to OCMD. Perfect for families and huge yard for kids to play. Washer & dryer a huge plus! The sunrise is amazing from the dock, just a short walk and you’re there. Our favorite was the moon over the water at night, absolutely stunning. We hope to go back next year! Best place we have stayed in a long time!

We travel a lot. We spend a lot of nights in all sorts of rentals. Egrets at the Point is a crown jewel. It’s not the fanciest place we’re stayed in, but it felt like home, and the comfort level is off the charts. This is not a museum, it’s a home. There was plenty to love about Karen’s home. There was nothing missing. And if there is, Karen or Chris are just a few steps away. The town of Onancock is close by, a short drive or if you like to walk and watch nature, it’s a short stroll. Karen can answer pretty much any question you might have after reading the guide available after you check in. Visit. You’ll want to come back and wish you had stayed longer. We know we’ll be back!

We loved this condo so much we extended our stay. Sherry was great to work with. Easy to find and clear instructions for checking in and out. The bed was super comfortable. The view was outstanding. It was so quiet and peaceful. We just loved everything about it. We would definitely stay here again the next time we are in the area.

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.

The place was immaculate, and everything was in working order. The property is beautiful. I will stay there again next time I come to town.

Joe and Kristi were so nice, the condo was beautiful! The view of the beach was amazing, you can see the beach from the deck and even from inside through the glass, if you’re having a couple hours of relaxing time between activities, the view and sound of the beach makes it still fun to be inside on vacation. Great space to sleep. It was an amazing place to stay for vacation.

Adam was a great host, answered all questions we had in a timely manner and went above and beyond to check in to make sure we were settling in and enjoying our stay. Our daughter loved the extra amenities of toys and the bunk beds. This home provided beautiful views of the sunrise on the beach and an excellent view of the sunset on the bay. We are already planning our next stay.

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!

AMAZING VIEW!!! It felt like we were right on top of the ocean. I loved the panoramic view you got from the master bedroom if you opened the curtains the lead to the balcony. Very clean and modern.

The view and easy access to the beach make this perfect for a weekend getaway. Quiet in the offseason and close to tons of great local restaurants.

This was a beautiful place to stay at with all the amenities you need! Check in and out was very easy and Corey Responded quickly with any issues or questions. Both beds were very comfortable. You had an immediate view of the bay walking out the back door, which was our favorite part! We would definitely stay again!

We had a great time at Seth’s place. The location was perfect, quiet but still plenty to do. Easy beach access and clear directions for everything. Watched dolphins from the balcony and loved hearing the waves.

This beautiful condo has a balcony view of the ocean, is away from the hustle of OC but close enough to enjoy the fun, and has semi-private beach access that makes for a great trip. We appreciated all the amenities and the cleanliness of the house. We’ll definitely be looking out for this place again next time we’re in town!