
Cottage holiday rentals in Assateague Island
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Top-rated cottage rentals in Assateague Island
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Popular amenities for cottage rentals in Assateague Island
Cottage rentals with a hot tub

New Waterfront Listing! Sleeps 7.
We enjoyed Kristen’s home it was so he perfect location for our itinerary on this adventure. Blessings - joe and Jen

Uncle Buck's
Uncle Bucks was exactly as pictured and described. The location cannot be beat either, having walkable access to the beach was perfect. A lot of amenities at the cottage as well, the hot tub being the best in my opinion. I had a nice relaxing week, which was the goal of my visit. Thank you again!

Coral Cottage-w/Guest House-Waterfront-Hot Tub
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.

Private point on the Bay🌤hammock, hot tub, kayaks❤️
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!

Year Round Playground - Rare Rustic-Modern Getaway
The house was very clean and very fresh smelling. Being in the woods surrounded by trees you can sometimes expect a musty smell, but that was not the case at all. The house was immaculate, and the rooms were very comfortable. The house was very quiet and private and the room was a nice touch. We all enjoyed the pool table. My husband did a lot of fishing at the dock and we also enjoyed the pool and the hot tub. We will definitely come back and stay at this house. Nadia was a great host. She mentioned that they are just starting out being a airbnb host, but you wouldn’t know it. The house had everything we needed.

Dog friendly *HOT TUB* Close to outlets, Sleeps 7
Great place for a small group gathering. Fantastic hot tub. Great space, stocked kitchen, plenty of things to do nearby.

Cropper Creek House
The house is spacious, clean, and conveniently located. Laura made everything simple, including easy check-in and good local tips. It was perfect and fun for four, but would comfortably accommodate more!

Beach Suite 2 King Beds Pet Friendly Canalside Inn
I was a bit skeptical at first because I've never booked a hotel room through airbnb. This experience was great. The suite was clean and I was able to have my pup with me. Located close to the beach and attractions. Great stay, would recommend.
Pet-friendly cottage rentals

ESVA Down by the Sea & Pet Friendly
This place was perfect for what we were looking for! We will certainly be booking again when we come back.

3-bedroom cottage in Ocean Pines
We enjoyed every moment of our stay. Viktoria was incredibly kind and the cottage was fully stocked. We came during the offseason and weather was not cooperative at first but we were able to use the board games, watch movies, and learn some origami on the wet days. We rode the bikes and my kids loved the nearby playground and basketball court. There were treats and bowls for our dog and the neighborhood was peaceful. We were able to go to Assateague Island a couple of times and the horses were a huge hit with everyone. Our dog enjoyed the beach, too. The only misunderstanding we had was thinking the community indoor pool was included in the amenities for free. There’s a user fee but we ended up getting a couple of nice beach/boardwalk days instead so it all worked out. Viktoria was quick to respond when we asked about it and sent instructions for how to access it if we chose to do so. This was a great time away from the city for all of us. We wouldn’t hesitate to stay again.

A "True" Chesapeake Bay Waterfront Experience!
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!

Monthly Rental w/ TONS of Storage! Please message
We had a very nice stay. Everything was very clean and nicely appointed. Our two doodles loved it too. Will is a very gracious host and we highly recommend him and his properties anytime you want to come to the Bethany beach area. We will be coming back very soon. Thank you.

Quaint Beach Block Cottage, 100 steps to the beach
Our family had a fantastic stay at the A’s by the Beach Cottage. The place was very spacious, on a very quiet street and literally steps from the beach. The well stocked kitchen had all that we needed and even more to be able to cook meals and enjoy family time at the dinner table or spread around the enormous kitchen island. The cottage had beach toys and chair, which made it even more enjoyable and relaxing to spend time at the beach all day. Inside the home, we found games that the whole family enjoyed as well. The kids loved bunk beds in one room while parents found comfortable beds in the other two rooms. We are looking forward to returning to this property later this summer for more fun and relaxation!

Cambridge Cottage
I absolutely adored this Airbnb! It was clean, adorable, and comfortable. I loved the aesthetic, but I will say if you have dogs, it would probably be safer to create them overnight. The spiral staircase was a bit difficult to maneuver for my larger guys. That’s not a problem at all, but just something to think about!

Once Upon A Tide
The cottage is very cozy and beautifully decorated. The beds were super comfortable. We had a very peaceful stay and got a lot of much-needed rest. The restaurants nearby offer great comfort food. Chincoteague was a little sleepy because it was off-season but that it what we were looking for. Stephanie is a fantastic host.

Charming Canal Front Cottage
This place is truly charming! The cottage was adorable and had everything we needed. When we arrived, the home was neat and very clean. The beds were extremely comfortable, and even though it is a cottage, we had plenty of room to spread out and relax. The neighborhood was quiet, and it's just a short drive to the Ocean City strip. Colleen was a wonderful host and we highly recommend staying here!
Private cottage rentals

Bayberry - awesome Solo Stove Fire Pit
Nice place I really recommend

ISLAND SUNSETS Near Chincoteague Island
Great, comfortable place to stay for a visit to Saxis and the eastern shore. Well-kept with all necessary amenities.

Cozy Cottage on the Bay
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!

Waterfowl Watch Chincoteague Cottage + BIKES
Great stay in a great location! Jennifer was very accommodating during our stay. She provided local recommendations which was helpful as well.

OV Central Beach Cottage
The house was exactly as seen on website would definitely stay again..definitely longer just to have a bbq and fire 🔥 easy to get to town..very quiet felt like home .i live in the woods in the hudson valley already showed my friends and family house 🏠 thank you so much 💓

Cozy Cottage Close to Downtown Built in 2021
We were in town for the Easter holiday to visit family, and John's cottage was perfect for our needs. The cottage is a very short drive to the boardwalk/beach and could easily be biked. Also within walking distance to a coffee shop and brewery which was great. The kitchen had everything we needed for cooking and eating meals. We travelled with 3 adults and 3 kids. Two of the bedrooms have ensuite bathrooms which was wonderful for privacy. The best part for our family is that we were able to travel with our 2 dogs. John's house was perfect for this. The fully fenced privacy fence in the back was so great and we enjoyed our time on the wonderful screened in porch while the dogs played. Would absolutely stay again!

Cozy "Waterfront Cottage"
The cottage is perfect. For a quiet getaway. We caught blue fish right of the pier. And cooked them same day. We had a great time. The weather was beautiful. Sunsets are spectacular. Thanks Debbie, you are a great host.

Country Cottage -7 Miles from Fenwick Island Beach
I was in the area for work and just had to look up this great place again, very excited that it was available for the dates i needed. When you're so far from home all you need is a little place that feels like home to help you get cozy amd relaxed after a hard days work. A few apdated additions since last time i sayed were very nice to see, the paved drive, the gravel walkway to the porch amd firepit and also the outside shower. Of all the places ive been to this is by far my favorite! Thanks so much again for the wonderful stay, im already looking foward to the next trip up :)
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