Cottage holiday rentals in Assateague Island

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Popular amenities for cottage rentals in Assateague Island

Cottage rentals with a hot tub

Guest favourite
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 favourite
Cottage in Dewey Beach
4.89 out of 5 average rating, 80 reviews

Uncle Buck's

BreezyRating, 5 stars3 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 favourite
Cottage in Woolford
5 out of 5 average rating, 64 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

TheresaRating, 5 stars5 days ago
Natalie was a wonderful host - the cottage was clean and welcoming and looked just like the photos. Natalie was very responsive, flexible and friendly. The river was peaceful and we enjoyed kayaking and fishing off the dock. We are very thankful we found such a perfect spot for our weekend trip to Maryland.
Top guest favourite
Cottage in Easton
5 out of 5 average rating, 106 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

MeganRating, 5 stars4 days ago
This is our second time visiting and a perfect spot with everything we needed. Could provide more dish towels, paper towels, and trash bags but supplies were provided quickly upon request.
Guest favourite
Cottage in Marion Station
4.71 out of 5 average rating, 38 reviews

Year Round Playground - Rare Rustic-Modern Getaway

BrittanyRating, 5 stars1 day ago
Had a mini friend vacation with 6 people total and we all immediately felt right at home. The layout of the home is extremely convenient-there’s a half bath next to the washer/dryer right near the door to the deck- it was perfect for fast bathroom breaks without getting the entire house wet! We spent most of our time in the pool area and game room, and both spaces had everything we needed! (Nadia, I hope you don’t mind we left a few pool new loungers behind!) We took advantage of pretty much everything aside from swimming in the lake (bugs were really bad, no one’s fault at all but be warned- you NEED to have bug spray.) The only critique I could give was the softness of the beds, they were all really firm and if you have any sort of sleeping and or back/pain problems, it could be evident the next morning. But overall it was an amazing time and the host was extremely courteous and genuinely caring! A lot of love goes into this spot and you can tell. We can’t wait to go back.
Guest favourite
Cottage in Rehoboth Beach
4.95 out of 5 average rating, 173 reviews

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

BeatriceRating, 5 stars5 days ago
This was our second time staying at JoJo’s cottage and it was another amazing experience! The house really makes you feel like you’re right at home. The kitchen is well stocked, so we were able to do a lot of cooking at the house. But you’re also so close to so many restaurants for when you’re feeling something easier! It really is a perfect spot, especially if you have dogs and/or kiddos. We would totally book again next summer 😊
Guest favourite
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars2 weeks 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 favourite
Cottage in Ocean Pines
4.93 out of 5 average rating, 46 reviews

Rhapsody in Blue Beach Cottage Ocean Pines, OC MD

WilliamRating, 5 stars4 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 favourite
Cottage in Saint Michaels
4.98 out of 5 average rating, 237 reviews

The Little Anchor Cottage, St. Michaels, MD

RoxanaRating, 5 stars6 days ago
Great home in a beautiful area. Spacious rooms and the whole house is equipped with everything you need. I love Airbnbs that feel homey and not ‘commercial’. The area is BEAUTIFUL and walkable with great restaurants near by (checkout limonchello and get the pizza!). Perfect for a weekend.
Superhost
Cottage in Chincoteague
4.72 out of 5 average rating, 100 reviews

SNUG HARBOR waterfront cottage with a grand view!

AlexandraRating, 5 stars2 weeks 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 favourite
Cottage in Ocean Pines
4.98 out of 5 average rating, 41 reviews

3-bedroom cottage in Ocean Pines

SylvainRating, 5 stars3 weeks 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 favourite
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!
Guest favourite
Cottage in Melfa
5 out of 5 average rating, 11 reviews

South Cottage at Vaux Hall w/Roll Up Garage Door

CatherineRating, 5 stars5 months ago
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!
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 favourite
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 favourite
Cottage in Oxford
5 out of 5 average rating, 17 reviews

Sailor's Cottage - Private Waterfront

ChristopherRating, 5 starstoday
We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.
Top guest favourite
Cottage in Lewes
5 out of 5 average rating, 30 reviews

Betsy's Guesthouse! New rec area, see pictures!

KarenRating, 5 stars1 week ago
My husband and I were impressed with Betsy from the time we made the reservation to the time we checked out. Betsy is as genuine as they come. She went above and beyond to make us feel welcomed, comfortable, and special! Betsy made sure we were well informed regarding local places to visit i.e., restaurants, etc. The cottage was absolutely perfect! It was exceptionally clean and beautiful ! We have stayed at many Airbnb’s over the years and we can honestly say that this was by far the BEST one! We’re looking forward to going back! Betsy, thank you for everything! Saul & Karen
Top guest favourite
Cottage in Onancock
5 out of 5 average rating, 53 reviews

Waterfront Victorian home in downtown Onancock

GoldyRating, 5 stars2 days ago
Beautiful home and just the right space for our family. Maggie was a great host and had all the items need for my grandson including age appropriate toys. This was our second stay and could not ask for a better place in Onancock.
Top guest favourite
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 favourite
Cottage in Selbyville
4.96 out of 5 average rating, 67 reviews

Country Cottage -7 Miles from Fenwick Island Beach

CindyRating, 5 stars4 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 favourite
Cottage in Selbyville
4.97 out of 5 average rating, 67 reviews

The Cove Cottage, West Fenwick

SuzanneRating, 5 starstoday
This home is exactly as described and then some! Cozy and warm, beautiful decor, updated kitchen and great outdoor area. No detail was overlooked. Joie was very responsive whenever we needed something. We'll definitely be back!
Guest favourite
Cottage in Deal Island Historic District
4.95 out of 5 average rating, 85 reviews

Private Beachfront Cottage with 2 Bedrooms + Loft

SuzanneRating, 5 stars1 week ago
Our family had such a lovely vacation in a great location. We made so many memories and enjoyed the beach and water everyday. Chelsea was a very responsive and accommodating host. So happy to have chosen their place for our vacation. The only draw back was the bugs but we were fully aware that they would be there as it was made very clear in the listing and in the reviews and it wouldn’t have changed our minds and we would love to visit again.

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