Holiday rentals with a kayak in Assateague Island

We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.

What an amazing place! The photos did not do it justice. We had beautiful weather and the back patio/deck was the perfect hangout. We went kayaking, caught a lot of crabs, and enjoyed being by the water. We had the firepit going while one of us was grilling food and the vibes were perfect. The detached game room saw plenty of heated pool games with a great selection of music and sound system. Bedrooms were comfortable and the kitchen was a joy to cook in. Dawn provided very detailed instructions so that you know all that you need to do. All-in-all, great spot that is a perfect group getaway!

The River House was phenomenal, a beautifully furnished place with large riverfront lawn and private boat launch. Exceptionally clean and well-stocked with everything you could think of for a comfy stay (fluffy towels, extra paper products, cleaning supplies, blankets, tons of pillows). Kitchen is as beautiful as the photos, and amply stocked with everything from ziplocs to pyrex to measuring cups and baking tools. The kayaks and canoe were easy to access and use. Easy place to paddle in a calm and quiet tributary. Highly recommend Lindy’s seafood a mile away. Host has compiled a guidebook with lots of local business recs and info. You will not be disappointed with a stay at this awesome retreat.

My wife is a bit of a planner so scheduling a last-minute getaway is not something I do often, but I'm so glad I did. This was exactly what we needed, A few days away from the stresses of life and family. This home met all of those needs. It was quiet, secluded and overall a very beautiful location and home. It had everything we needed and more. The small towns of White Stone and Kilmarnock offered many fantastic food options which we definitely took advantage of. I would definitely recommend this place to friends and family. We have already started looking to see if we can plan a trip here with the whole family. Thanks again to our host who was very responsive and helped answer all of our questions.

First of all, this house and the views are STUNNING. This was the first vacation that I have taken with my fiancé and our 2 pups, and we had the best time--it was such a sad day when we had to leave lol. We basically ordered Doordash and Walmart Pickups the entire time we were there and never left the property during our stay. The kitchen was very well stocked with all the cookware you could need, there are kayaks and paddle boards for entertainment, and plenty of floats for relaxing in the bay. There is a little private beach within 1 min walking distance from the house and there is access to the water from the backyard. It had everything we wanted for a relaxing vacation with our pups. I am already working on convincing my fiancé that we need to go back in the near future. 10/10 would recommend.

Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!

The Haven on the Bay is an incredible property - we stayed here last year and loved it so much we had to stay here again. And this won’t be our last time - we plan to make it an annual trip at a minimum! Ashley is an amazing host and ensures her guests have a fantastic experience! Stay at this property - you won’t regret it.

Janice’s house was lovely! Great location. It looks just like the pictures. The view from the living room and back deck is stunning. The house was very tidy. Janice communicated well and promptly. The only disappointment was that there is no screen door in the master bedroom, and therefore, I couldn’t enjoy leaving the sliding doors open, which I love to do when staying in a waterfront home. Otherwise, we had a wonderful stay! Would definitely recommend!

Wonderful little A frame beach cabin feel. Timothy is very helpful and responsive. We did the dogfish dash and was the perfect little place to stay the night before our run. There is only 1 bathroom which wasn’t ideal in the morning for 4 people, but everything else is amazing!! Highly recommend :)

Took my adult siblings and parents to Taryn’s property & everyone has already asked “can we go back next year?” The seclusion, water views, and acreage to explore was incredible. We were excited to take our dogs who loved running through the marsh out to the beach. Yes, there’s a lot of flies and ticks due to the marshy area, but we brought plenty of bug spray and checked the dogs each evening for ticks. Definitely recommend catching a sunset on the beach. No frills, no fuss..lots of fun & no-phone-service family bonding time.

We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.

Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.

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.

It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.

Mystic Is a quaint, clean and welcoming houae. All details from pictures to knick knacks create a complete theme. Instructions were easy and thoughtful. Communications were prompt and thorough. This home and its owners create a perfect sanctuary.

Andrea's cottage on the Chesapeake Bay is a jewel in the Northern Neck of Virginia! We spent a long weekend here with our pup and we enjoyed every minute of it! The home itself is gorgeous; it was tastefully decorated, free of clutter, featured extremely comfortable furnishings and was equipped with everything we needed. But the piece de resistance was the view of the bay from the sunroom. We sat in that room for hours just gazing at the waves, the ships in the distance and the variety of birds including herons, cranes, seagulls and pelicans. We also saw a dolphin swim by! The view was perfectly stunning! Andrea was also the most gracious host. She reached out to us before we arrived to tell us about a few places to visit and things to do during our stay. She was quick to respond to any questions we had and we felt as if we were being cared for by a family member! Be sure to visit this cottage on the bay; you won't regret it! Thank you, Andrea, for a wonderfully serene weekend!

Great place for a getaway! St. Michael’s is a wonderful town and so easy to get to from this lovely place! Was perfect location for our family ladies trip- plenty of space and just a quick trip down town to the shops and restaurants! - I think we’ll be back!

We enjoyed our stay here. Very quiet area, nice comfortable space. The gravel road leading in (maybe a half-mile long) and driveway gave us a good area for morning and evening dog walks. We did not end up doing any fishing but the pond looked like a great place for kayak fishing. Not specific to the house but in the area: Rita's Cafe in Weems was great (food truck on a small road)--Chef Craige usually has a special and some regular menu items. Leadbellys (at Fairport Marina) had good oysters and hush puppies and was convenient for our first night. River Market in White Stone has good food to be ordered at the rear counter and prepared items in the coolers. Out of the Oven Bakery (White Stone) had great bread Miss Mary's seafood, also in White Stone had great fresh fish and prepared items. The three places in White Stone are very close to each other so convenient when running out.

Our stay at the Bateau Cabin was absolutely magical. Nestled in serene surroundings, the cabin feels perfectly tucked away while still being close to everything you could need. Elizabeth is the most gracious and thoughtful host—her attention to detail makes the experience truly special. The cabin itself is perfection: modern yet incredibly cozy, with every amenity you could want. The kitchen is a dream for anyone who loves to cook, stocked with All-Clad cookware and beautiful dishes. There are bikes and kayaks available for exploring, and the hammock is the perfect spot to peep nature or dive into a book. Sunsets and sunrises are pure magic, and the entire experience feels like stepping away from civilization—fully immersed in nature and surrounded by peace. It was the perfect retreat for us, and we can’t wait to return! Thank you Elizabeth for hosting us.

We stayed for an annual ladies' trip. I loved the peaceful views from the porch and kayaking by herons. My friends got a kick out of catching and cooking crabs for the first time. When I asked about a crab pot for cooking their hoped-for haul, the hosts ordered one for delivery right away. Great place to hang with friends, but I'm sure my kids would also love the firepit, the dock, and the kayaks. Thank you!

Our experience at Ted and Jen's house by the beach was amazing. We enjoyed it so much! The house was clean and comfortable, with all the little touches like a basket of snacks and a can of bug spray. Ted and Jen were amazing hosts. From meeting us at the ferry, to showing us a little tour of the island on the way to the house, to giving us pointers on how to enjoy the area, Ted and Jen gave us the full Tangier Island experience. We expect to make this a yearly summer tradition!

I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.

This place was as described. Very peaceful get away for my family and totally worth the price we paid. Teresa was quick to respond and recommended some place to eat. We will be back to experience the fall weather.