
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
We had a wonderful stay at Uncle Buck’s. Our only problem was the stay was too short! Lisa made the place feel like you were borrowing a friend’s house for a few days. She was very responsive to the few simple questions we had. We are already looking for dates for another visit. As an aside, we met a good friend of ours for a drink when we got home and when we showed him pictures, he immediately recognized it. It turns out he had stayed there with some other friends of ours a few summers back.

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.

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.

"Bayside" Coastal Cottage w/ Golf, Hot Tub + EV
We enjoyed this beautiful property very relaxing and peaceful, located within a golf course. The beach is 10 minutes away, there’s also great food, attractions, arcades, miniature golf and tons of fun activities to enjoy as this property is on the boarder. Rebekka was an amazing/accommodating host.
Pet-friendly cottage rentals

3-bedroom cottage in Ocean Pines
Viktoria's place was perfect for what we needed for our stay in Ocean Pines. She was very responsive and accommodating.

A "True" Chesapeake Bay Waterfront Experience!
Matt was a great host and helpful. The house was great very clean with plenty of room. The veiw of the water was nice. I highly recommend if you are looking for a nice weekend getaway.

Rodo Beach Cottage - Dog Friendly Private Beach wi
Place nicer than advertised. Although we only stayed 2 nights we definitely had a good time. The private beach was amazing and overall the place was very relaxing. My only complaint would be to make the pet fee as part of the booking process. My own fault that i didn't notice that after booking in the details.

The South Cottage at Vaux Hall Farm
What a truly special place Vaux Hall Farm is! The cottage and location couldn’t be nicer. Thanks to Eric for the warm hospitality too!

Cottage on Prentice Creek, PA
I cannot find the words to express our families stay. When I say this was the best stay at an ABNB we have had thus far it was. The outside itself from the landscaping to the scenery was breathtaking. Checking in was a breeze. Once inside pictures cannot begin to show the beauty of this property. The hosts have really thought through a guest experience. They went over and beyond hosts duties adding extreme attention to details. Anything and everything you may need or want for your stay was there. Even with all the extra amenities and the beauty of the home our family instantly felt at home. We loved our stay so much we have already booked our next stay.

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!

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

Deer Track-Cozy Cottage, Close to Town, Firepit!
We enjoyed our visit to Deer Track in Chincoteague. The cottage is clean with listed amenities. We really liked the quiet neighborhood it is located in.

ISLAND SUNSETS Near Chincoteague Island
Was very pleased! Super clean! Couches were cozy. Bedrooms were clean and comfy. Overall great stay! Will be booking again for future duck hunting trips.

Martha’s Cottage•at Old Beauchamp Homestead•
It was a peaceful and quiet weekend getaway. The house was cozy and perfect for our trip. We can’t wait to come back and visit again.

A-mazing Beach Cottage on Canal & Trolley Route
We flew in for a funeral and Elisha was caring and understanding of our late arrival. The only suggestion I would like to see as an option is sheets on the beds and 1 towel per person minimum already on premise - There was a topper upstairs that helped give support on the twin mattress downstairs, which helped our daughter sleep. Other then that, the space was clean, organized, and the beds were comfy, spring/coil which we needed. It was a quiet neighborhood, close to the canal, tennis courts, church, and main road

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!

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!

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!

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.
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