Pet-friendly vacation rentals 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.

Highly recommend! The setting on the river is so beautiful and charming. The house was immaculate and very well equipped so very very comfortable. The host were friendly and accessible to everyone want or question.

Thank you for another great stay!

We’ve stayed here twice. The house is clean and homey. Ryan is responsive and helpful. This location and house is especially nice for families and pet owners. We spend much of our time in the fenced backyard grilling and playing with our kids and dogs. The streets are great for long walks. Friendly neighbors. I give Ryan and his home my highest recommendation.

Stayed here for the weekend while attending Ocean City's Boardwalk Rock festival. Location was great, not too far away from the beach and house was tucked away in a nice quiet neighborhood. Everything was clean and looked as expected. Overall very happy will be back again!

This cottage is absolutely beautiful! Perfect for a couple or family. Honestly it’s so much nicer than the pictures, it’s bigger than I thought. Such a clean place to stay also. The deck is absolutely beautiful, we sat out there every morning and evening and watched deer! They even had a water bowl for our fur baby. It is so close to ocean city and Bethany beach!. You will not be sorry staying here, I’ll just say that!! Thank you Jay for letting us stay at the Lighthouse Cottage, we will always Remember our experience there, we will be back!❤️

Amazing Host and house exceptional friendly nice and so welcoming. beautiful views of the water and surrounding areas just an amazing experience and people thank you 🙏

Christy's Cottage was very comfortable and pet friendly. It was close to everything we wanted to do, and the kitchen was fully stocked. You can tell why she is considered a Superhost. We enjoyed our stay there, and would certainly consider returning. If you are going to see the ponies, we recommend Captain Mike with Up The Bay Pony Tours. Chincoteague and Assateague are lovely places to visit. Bring your camera if you are a nature lover. Pets aren't allowed on Assateague Island (not even in your car), but at Christy's we were able to leave our pups in their crates for a little while so that we go.

The apartment is beautiful, very comfortable, and fully equipped with everything you need for a great beach vacation. We had a lovely stay and really enjoyed the space.

Great deal and pet friendly! Responded when I needed something within seconds and answered any questions I had. Clean and beautiful! Thanks again!

Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Absolutely cutest rv and unique setting ! We had a blast. We went to the Tiki bar, great dog park in Kilmarnock and many walks along the shore. We even saw a bald eagle fly over us while we were drinking our morning coffee! Everyone we met human and dog was super friendly! That made the trip extra special. Morgan is friendly and a great communicator. Her rv was spotless! Hope to get back to stay another time. Take care Morgan! You have a gem! 💎 ✨ Keep shining! ✨

The house inside was gorgeous. We loved the natural light that came from the many skylights. The kitchen was appropriately stocked with coffee and condiments and plenty of cooking utensils to fix ourselves breakfasts and lunches. The yacht club was very close to the house and convenient for an evening dinner outside.

This was our first time staying in Ocean Pines. We thought Kristy's place was in a good location and an easy drive to Ocean City and other surrounding areas. Since we enjoy the outdoors, we loved hanging out on the screened porch and the fenced backyard was great for our little dogs. The neighborhood was surprisingly quiet and we enjoyed walking along the scenic trails. The inside of the home was nicely decorated and we felt there was enough space for our family of four (2 adults and 2 young adults). We liked the helpful information and flexibility that Kristy offered.

I had a great stay! The condo was in a perfect spot—just steps from the boardwalk—with beautiful ocean views. It was peaceful, relaxing, and an excellent place for a getaway. Everything was clean, well-appointed, and comfortable. I’d definitely come back!

Private Oasis! This property has beautiful home has a private pool and large deck lovely decorated. This property accommodates a large group comfortably. Loved Extra Large Hot Tub! ❤ Walking distance to the bay, restaurant/bar and close to other attractions. Worth the money! The host is very thoughtful, responsive, and professional. This property is a gem! Fantastic Experience! Thank you

We ABSOLUTELY loved our visit, and plan to return and stay with Basia! Our weekend consisted of rainy weather and she offered us a covered porch which was well worth it!! Each morning we had a peaceful water view with the horses in the distance. I don’t think it could get any better. The boat tour was SO much fun. Basia stayed in contact with us about when would be the better time to go. She really looked out for us when the weather would be at its peak. Her recommendations never failed to impress. Thank you SO much for having us!! We plan to be back.

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!

We had a lovely time at the Rusty Anchor! Christina was a wonderful host and very responsive. There were no issues throughout our stay and we had an overall wonderful time. The place is very quaint and cute. Definitely more remote so if you’re looking for an active area this isn’t the location. But it was so nice for a private getaway!

Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

We were able to check in earlier which was great tho some of us weren’t able to get there right away… we enjoyed our stay very peaceful and were wishing we could have one more day! 😊 we were going to grill burgers but couldn’t find grill utensils so just did our best inside and still turned out great!!! Thank you for your house and allowing us to stay there!

We loved our stay in Captain’s Cove! Nick was a very responsive host with wonderful local suggestions. Do be aware that there is really not much in the way of gas stations, grocery stores or restaurants in the immediate area. We knew that going in, though, and it wasn’t an issue for us. Just know you will need to drive a bit or prepare with those items on your way in (which Nick told us in advance as well!) The view is beautiful! The Airbnb is exactly as pictured. It was very quiet as well. Loved that it was pet friendly so we could bring our dog! Would definitely stay again!

Perfect getaway from the city. The cottage is both modern and cozy, and the property is beautiful and dog-friendly. Clean and well stocked too. 20 minute drive from most local attractions. Rod and his family are great hosts. They were on site when and available when needed but otherwise let us have our privacy.

From a fellow renter, Chantell was a very responsive host. She was quick to answer any question and took care of our needs quickly. Her house quickly felt like home. It was decorated with modern amenities yet still felt warm and cozy. We lacked for nothing during our stay. It was just the peaceful place we needed after spending the day at the local convention center cheering on our son in sports. While everyone else stayed at loud hotels, we were just 20 minutes away from the ruckus and able to get the rest we needed. This home comes highly recommended.