Cottage vacation rentals in Assateague Island

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Popular amenities for Assateague Island cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Bethany Beach
4.94 out of 5 average rating, 17 reviews

Bethany Beach Sea Colony Canalside Sleeps 7

JosephRating, 5 stars3 months ago
We enjoyed Kristen’s home it was so he perfect location for our itinerary on this adventure. Blessings - joe and Jen
Top guest favorite
Cottage in Dewey Beach
4.89 out of 5 average rating, 80 reviews

Uncle Buck's

BreezyRating, 5 stars2 weeks ago
My friend and I loved staying at this little house. It was so close to the beach, the hot tub was amazing in the evenings and the house was comfortable and welcoming. It was clean, organized and well stocked with the towels. Great little getaway spot at a wonderful price.
Top guest favorite
Cottage in Woolford
5 out of 5 average rating, 63 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

MalgorzataRating, 5 stars3 months ago
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.
Top guest favorite
Cottage in Easton
5 out of 5 average rating, 105 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

LindsayRating, 5 stars3 weeks ago
From start to finish, Cheryl and Tom’s property made for the perfect weekend in the St. Michaels area! Clear instructions, absolutely gorgeous property/amenities/activities - it is an absolutely jaw dropping property. Our only regret was not staying longer!!! Thank you!!
Guest favorite
Cottage in Marion Station
4.7 out of 5 average rating, 37 reviews

Year Round Playground - Rare Rustic-Modern Getaway

JaniceRating, 5 stars9 months ago
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.
Guest favorite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 171 reviews

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

DaveRating, 5 stars1 week ago
We loved our stay at Jojos cottage! It is so homey and inviting. The house has everything you could possibly need for a comfortable stay and it is so close to restaurants, shops, and the beach. Joanna was a wonderful host, very responsive and helpful from day one. We can’t wait to go back for our next stay!
Guest favorite
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars1 week ago
We LOVED our stay! The screened porch overlooking the beach was so peaceful and our favorite place to be in the evening. The house was lovely, well cared for, very clean, and very tastefully decorated. The welcome book provided everything you needed to know about the house and surrounding area. We will be back again!
Superhost
Cottage in Lewes

Lewes beach family cottage

YevhenRating, 5 stars11 months ago
We were the very first guests in Eric’s house and we thought Eric did a good job to prepare for his first guests. There are still a few things to improve but I’m sure those will get improved with time. Overall, this is a great house in a very quiet neighborhood. Only a few miles away from the beach. There is a full size on the ground pool that is pretty new and it was a nice surprise especially for kids. Kitchen has everything you need and maybe more. We’ve had a few issues in the beginning but Eric was real quick to respond and help resolve the issues. Additionally, he was checking in sporadically through our stay to make sure everything was going well. We thought it was a good value for a house in Lewes during very busy season. I would recommend anyone looking for a stay in Lewes to give this house a chance.

Pet-friendly cottage rentals

Guest favorite
Cottage in Ocean Pines
4.93 out of 5 average rating, 46 reviews

Rhapsody in Blue Beach Cottage Ocean Pines, OC MD

WilliamRating, 5 stars3 weeks ago
Everything you would need! Linens, coffee, all kitchen utensils and appliances. Easy entry. Super cool AC! Nice quiet neighborhood. Clean and cozy. Very happy. Thank you!
Top guest favorite
Cottage in Saint Michaels
4.98 out of 5 average rating, 234 reviews

The Little Anchor Cottage, St. Michaels, MD

GillianRating, 5 stars3 weeks ago
This was now our second time staying here and if possible, it was even better than the first. The hosts are so welcoming and the house is fully set up with everything we needed. The location is just a dream as well with easy walking access to all the restaurants and shops of this charming town. A great stay for the whole family.
Superhost
Cottage in Chincoteague
4.72 out of 5 average rating, 99 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars1 week ago
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.
Superhost
Cottage in Wittman
4.87 out of 5 average rating, 151 reviews

Perfect St. Michaels Getaway

SamRating, 5 stars1 month ago
This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.
Top guest favorite
Cottage in Ocean Pines
4.98 out of 5 average rating, 41 reviews

3-bedroom cottage in Ocean Pines

SylvainRating, 5 stars1 week ago
Viktoria's place was exactly what we were looking for. A three-bedroom place not far from Ocean City and Assateague, in a peaceful environment. Was super easy to go to both places during the long Week-End. The house was as advertised, spacious enough to accommodate the family but not too big. Next time we plan another WE in this area, we will certainly Viktoria's place again.
Guest favorite
Cottage in Lewes
4.87 out of 5 average rating, 201 reviews

BnB’s Dog-Friendly Cottage

SydneyRating, 5 stars1 month ago
Jacki's home was so lovely and perfect for a weekend getaway with some friends. We brought our dog who absolutely loved the fenced-in yard and extra loved the mountain of toys stocked in the house!
Superhost
Cottage in Painter
4.89 out of 5 average rating, 93 reviews

Cottage by the bay (private peaceful surroundings)

JorgeRating, 5 stars2 days ago
Very secluded but I don't mind that all. The home is beautiful and the host is very attentive.
Superhost
Cottage in Dewey Beach
4.89 out of 5 average rating, 203 reviews

Quaint Beach Block Cottage, 100 steps to the beach

MariaRating, 5 stars1 month ago
We loved staying at 14 Carolina Street! The house was great and was a very short walk to the ocean! Kelly and Thomas were very responsive and friendly! This home was a great location, would definitely come back again!

Private cottage rentals

Top guest favorite
Cottage in Ocean Pines
4.96 out of 5 average rating, 27 reviews

Cozy Cottage near the Ocean and Wild Horses

VivienneRating, 5 stars9 months ago
House was very clean and cozy. Everything is labeled and easy to find and Anne was very responsive with questions l had. The location is quiet and great for walking or bike riding. Restaurants are super close and so is the grocery store. Beach and other cute towns such as Berlin and Snow Hill are very easy to get to as well. We had a wonderful time staying at Anne's place.
Top guest favorite
Cottage in Ocean City
4.99 out of 5 average rating, 69 reviews

WalkToTheBeach! FirePit-PingPng-N64-FencdYrd-Bikes

ShontayRating, 5 stars4 weeks ago
My family enjoyed our stay at the Blue House for a weekend getaway! The Host, Neil, allowed us to check in early, which was very much appreciated. The parking is right in front of the house. The check in was easy, after we realized you have to go through the back to access the entry door. The home was clean and we were very comfortable in it, especially the beds. I was able to prepare several meals and my husband prepared some bbq on the grill one evening. There are 5 bikes available, but only my younger son and I rode 2 of them around the neighborhood. The beach is only a few blocks away and easily assessible. I wanted to play ping pong, but couldn't figure out how to set up the table net lol. The host was very responsive and regularly reached out to make sure we were ok. He event sent us over some of the most delicious, warm donuts one morning. Overall, our experience was exceptional and we would love to stay there again next time we visit Ocean City!
Guest favorite
Cottage in Onancock
5 out of 5 average rating, 44 reviews

Sea Glass Cottage - The best relaxation vacation.

CherylRating, 5 stars3 months ago
Sea Glass Cottage was a delight! The house was very clean, bright and totally charming! Doris has everything you could need for a couple nights or extended stay. I would suggest everyone who stays read her "Welcome" book. She has great suggestions for dining, sightseeing, art galleries, etc. Beds are comfortable and the bathroom is VERY large. Onancock is a fun, charming town to visit. We will definitely return and, if Doris will have us, we'll be staying at Sea Glass Cottage. Thanks Doris for a great visit! Cheryl and Jerry
Top guest favorite
Cottage in Onancock
5 out of 5 average rating, 52 reviews

Waterfront Victorian home in downtown Onancock

NazaninRating, 5 stars2 weeks ago
We enjoyed our stay. The house had all the comforts of home with a well stocked kitchen. The bed was comfortable. We are looking forward to coming back.
Top guest favorite
Cottage in East New Market
4.95 out of 5 average rating, 63 reviews

Cottage on Cabin Creek

MicheleRating, 5 stars1 month ago
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.
Top guest favorite
Cottage in Deal Island Historic District
4.94 out of 5 average rating, 16 reviews

Cozy "Waterfront Cottage"

JohnRating, 5 stars9 months ago
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.
Top guest favorite
Cottage in Selbyville
4.95 out of 5 average rating, 66 reviews

Country Cottage -7 Miles from Fenwick Island Beach

CindyRating, 5 stars2 weeks ago
You will not be disappointed if you’re looking for a nice peaceful getaway but only minutes from the beach. Pop pops Place is so clean and cozy you would think you were the first renters! Stephanie is very thoughtful and has thought of just about everything and even left us Fishers Popcorn (local fav) to enjoy upon our arrival. It looked exactly like the photos and as described, if not better.
Top guest favorite
Cottage in Selbyville
4.97 out of 5 average rating, 66 reviews

The Cove Cottage, West Fenwick

JoshuaRating, 5 stars2 weeks ago
Stayed here for a few nights during boardwalk rock. Love this little cottage!! Peaceful community. Easy access to Rt. 54. Very clean and updated. Joie is a wonderful host!! Thanks again!

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