Holiday rentals with outdoor seating in Assateague Island

We had a great time in Chhaya's cottage. Very clean and well equipped. Conveniently located within walking distance of amenities. Perfect to go an explore Chincoteague Island and the Assateague shore.

Felt right at home from the minute we walked in and so did our pup! It’s very dog-friendly, they even have dog bowls out if you need them. There was a big thunderstorm at night and the house felt sturdy and peaceful. Also very comfortable pillows and bedding. I would recommend bringing an extra blanket if it’s colder out because the quilts are light summer-weight. Beautiful and private backyard, very nice and welcoming place.

We love coming to Georgetown and love staying at Rick's place. It's perfect for us, and we can relax there. The house is beautiful with great amenities. My mom appreciates the walk-in shower. The kitchen is fantastic for cooking. The beds are comfortable, as is the furniture in living and dining rooms. Rick is a fantastic host. I highly recommend this home!

This was our second time staying at this rental and we would recommend to others. Ann's communication was great and she even gave us the option to check in early and check out late as it was available.

We stayed at this house for a short break to visit Chincoteague Island, and it was a wonderful experience. The house was very clean and nicely decorated with a relaxing beach vibe. It had everything we needed for a comfortable stay. The host was incredibly responsive and welcoming, which made us feel right at home. The location is great—close to beautiful beaches, the wildlife refuge, and many good food spots nearby. We would definitely stay here again and highly recommend it to anyone visiting the area.

me and my wife stayed here with our 2pups willow and mazie. place was AMAZING for the dogs. fenced in back yard in and wrap around front porch that we ALL could enjoy neighbors were wonderful people and Dog lovers ❤️. James was a GREAT HOST. we actually got to meet him in person. I wish we could have spent more time talking. locationis KEY. run the dogs at fenwick beach then hop down downtown to plenty of restaurants and bars...we will definitely be back...thank you james

Returning to the Jungalow for a second stay within a few short months was deeply meaningful for us. Courtney’s warmth and attentiveness created an environment that felt both comforting and nurturing during a very personal visit. We came to celebrate the memory of our late dog, who had relished the backyard here on our last visit; bringing her ashes to the nearby beach felt like the most fitting farewell. Courtney’s kindness and the cozy, dog-friendly ambiance made this home an ideal setting for reflection and solace. The Jungalow itself is beautifully curated, offering a blend of comfort and aesthetic charm that feels both welcoming and inspiring. Every element of the space reflects Courtney’s dedication to detail and hospitality, making it a space that is as inviting for guests as it is friendly for pets. This home is truly a sanctuary, and we are immensely grateful to have returned. We cannot wait to visit again and experience this perfect, tranquil retreat once more.

We had a great trip to Bayside at Jeffrey and Deb's house. The house is conveniently located in a private peaceful part of the Bayside neighborhood, which has great amenities and is very easy to get around by walking or biking. The house was a perfect size for our family of 5 and was in great condition and we loved the screened in porch area and patio which backed up to woods. Jeffrey was also very responsive and was great to deal with. We would definitely stay here again. Highly recommended.

The place is super peaceful, clean and really comfy. I will stay there again for sure!

Felt super comfortable there. Everything was in walking distance beach, great restaurants bars and we even utilized the kitchen for breakfast and lunch. Loved the coffee set up and the quite seating area on the water out back. We def would recommend and would love to stay again!

It was a wonderful experience staying at Carla’s. The location is perfect. It is quite center in town. We loved the little apartment, it has everything we need. We would love to come back again!

Very roomy condo and easy walk to beach and beautiful canal views. Lots of restaurants, Jolly Roger, boardwalk and bike rentals all with walking distance. Best part is that it was dog friendly too.

We had a winter visit and despite it being freezing outside the house was nice and toasty and we appreciated the fast hot water for showering. No fenced yard for our dog but it's a nice area to walk around. Central location, close to restaurants. Would stay again.

Very nice family space. Nice area to play games or watch movies on the rainy days. Kathy was super helpful with parking and getting settled.

This was my second time staying at Judy's for an organized bike ride, and it was as amazing as my first visit. It is a safe, comfy cozy space for a solo traveler - you feel the Ocean City vibes with a bit more peace and quiet. The parking is convenient, it's easy to come and go, and I always sleep so well and enjoy waking up to the sounds of birds. Not only was it perfect for my bike ride, but it's also so close to Ocean City, the boardwalk, great restaurants (like Sunset Grille!), and other shops/outlets. Judy is friendly and welcoming - thanks again for a wonderful time and I hope to make it for year 3 next spring, if not sooner!

Great place to stay if you want to be near the nightlife but still private. Everything was perfect and I would 10 out of 10 get back again.

This was a great place to stay. It's on the north end of Ocean City, so we'll removed from a lot of the touristy stuff. Really great access to the beach that had lots of open space and absolutely no crowding. The place was well appointed and very comfortable.

Very nice place with enclosed patios. Neighbors were very friendly.

This is a cute place that is right on the bay so you can enjoy beautiful water views yet it’s an easy walk to the beach. The unit is nicely furnished. The shower with multiple jets was great. We appreciated being able to bring our small dog. We also appreciate the welcome bottle of wine!

This is the 3rd time we stayed with Kendra and it was a pleasure as usual. The location of the condo is great within walking distance to restaurants, mini-golf and the beach. It sits in a quiet neighborhood. The condo is well furnished and has all the comforts of home. Highly recommended!

Awesome place and great location for all OC activities!

Simple check-in and easy access. Not much to say besides the stay was very enjoyable and would recommend to any others! Had a great time with my friends.

This was the perfect place for our weekend getaway! Heather was super nice and responsive and her place was so cute and exactly like the pictures. It was walkable from multiple restaurants/bars and the beach and had a nice view of the water from the deck. If you wanted to go to any other restaurants that weren’t walking distance, they were only a short drive/uber away. We had such a great experience and will definitely be reaching back out to Heather when we come back down to visit to stay here again!!

Jodie has the most perfect Airbnb. It’s beautifully decorated, extremely clean and in a perfect location. She’s also very responsive and accommodating. I would definitely stay here again.