Holiday rentals with a kayak in Assateague Island

My absolute favorite airbnb ever ! This was the 3rd time I've stayed here, and if I could afford it, I'd go monthly. The location is perfect, right on the water, small private beach, lots of privacy and soooo incredibly relaxing. The house is very well laid out, super clean and comfortable. Keri provides more than most hosts, from the kitchen and bathrooms, to beach gear, movies, books, games, and the kayaks ! I love love love this house and location so very much. It feels like "my" home away from home and I'll continue to go back as much as possible. THANK YOU again Keri, for another amazing getaway !

Went to location as a family get-away. The views were breathtaking, who knew we would find such peace so close to home. Literally sat on the couch and stared outside for hours. The home was small enough to enjoy each other's company but large enough to allow everyone the time and space to do their own thing. The price was more than reasonable and we can't wait to return.

We had a great time visiting onancock and Kimberley's place was a cozy home away from home in a beautiful setting, right across the street from the water.

We had the most relaxing stay at this wonderful property! It truly had everything we needed. The outdoor shower was a highlight, complete with shampoo and conditioner for both humans and pets—such a thoughtful touch! The place was stocked with firewood and a starter kit, which made our evenings by the fire so cozy. Our family loved kayaking and fishing nearby, and the tables were perfect for some fun card games. The kitchen was fully stocked with all the essentials, including seasonings, and there were even pet bowls for our furry friends. We couldn't have asked for a more comfortable, well-equipped getaway. Highly recommend for anyone looking for a peaceful, all-inclusive retreat!

Dawn’s place is the nicest Airbnb we have ever found! I never experienced a house where there are so many extras to make your visit special! Dawn and her husband have gone above and beyond to create this peaceful dog-friendly oasis. The game room was a blast, the dock and patios were comfortable with chairs, cushions, lounges and a fire pit. Dawn even supplied graham crackers, marshmallows and chocolate to make Smores! The beds were super comfortable and there were tons of towels for people and pets. We also enjoyed the deep bathtub, bubble bath and shower. It was go great not to have to bring shampoo, body wash and all this much need toiletries that fill your suitcase. My family had a relaxing fun week there and will definitely be back. I wish we could give a ten star rating because that’s what this place deserves! Thanks Dawn 😇

Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!

We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

Where should we begin? Lucas and Heather were wonderful hosts. Excellent and quick communication. Their home has been thoughtfully curated with top notch, kitchen appliances, bed and bath linens, entertainment amenities, and more. Even on a cool and rainy day, you can sit around the fireplace, listen to music, play games and look out the window to a stunning view of the water. No stone was left unturned. This is indeed a special place in the lovely little town of Oxford. We hope to stay again. Thank you, Lucas and Heather for the exceptional hospitality.

Jessica and Richard were very welcoming and friendly. Place was great right on water. Very private. Grandson and I fished off dock with good success. J&R lent us a crab pot and we had a blast.

A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.

With 180 degree water views, what could be better?! We saw birds, incredible sunrises over the bay, and enjoyed sunset in the hot tub. It’s just right for a long weekend getaway to relax and unwind!

My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!

I truly wish I could put into words just how beautiful and peaceful this home and property were. It is truly a place that was so inviting and well maintained it made me miss the eastern shore of Virginia and start looking at properties in the area. The land is so cool to walk and explore and the bay at this home is just serene. To be able to wake up and see the view this home has is just spectacular. Matt is spot on with the description of his home and you truly can't find one thing wrong with this home or the property surrounding it and having a dog,it is so key with the wash station outside because our lab puppy could not get enough of the bay or going out in the kayaks with us. I truly wish they had more stars to rate this home. Thank you for being so gracious and allowing us to visit your spectacular home!

This was our 2nd stay on the island , but first time at Mary Kim's. Great hospitality including home cooked egg rolls that made the long journey even more worth it. The only downfall would be the dock and kayak spot is a couple doors down, but Mary Kim was very communicative. lastly, I highly recommend the golf cart service on the island, gives you more of an ability to explore the island.

We would highly recommend this peaceful and relaxing cottage. We especially loved the views, the dock for fishing, & the views from the bedroom. Janelle was very helpful with places to visit as well as working out an issue that came up at the property. She was quick to respond & made every effort to make sure we were comfortable. Would definitely stay here again! 😊

The cottage was a perfect place for a relaxing anniversary getaway. Beautiful views, peaceful setting. House is very well maintained, clean and comfortable. Easy to launch canoe /kayaks from the dock, campfire by the water watching the moonrise over the water. Perfect, would love to return. Highly recommend.

Had a great one-night stay! The cabin was clean, comfortable, and just as described. Check-in was smooth, and the host was responsive. Perfect for a peaceful getaway—would book again!

Had a great time at the Elderberries cottage! The views were spectacular, and you could take them in from the enclosed porch, the open deck, and even the living room. The entire setup was perfect for a vacation/remote work getaway, and the kitchen has everything you need. WiFi worked great, and the smart TV supported pretty much any streaming service you'd want. Rachel was friendly and super responsive; we hope to stay there again sometime.

This is a wonderful place on a large creek off the Chesapeake Bay. This place oozes with charm and ambiance and feels so peaceful. We spent the first day just relaxing and doing nothing but looking at the water and chilling on the front porch. The house is updated on the inside and has a large lot with kayaks and a fishing pier. Great hiking at the natural preserves in the area too. We're grateful to the hosts for opening their home to us and we'll definitely come back.

Great place to stay for rest, relaxation, peace and quiet. In my short time there, I saw a wild turkey, a fox, an otter, red wing black birds, a woodpecker, and cardinals. And at night, I heard tree frogs and an owl was really close by. Terri is wonderful as a host!