Waterfront holiday rentals in Assateague Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for waterfront rentals in Assateague Island

Waterfront apartment rentals

Guest favourite
Flat in Ocean City
4.88 out of 5 average rating, 8 reviews

StayAhoy! | Steps to Beach | Ocean View

MattRating, 5 stars1 day ago
Fantastic stay for my wife and I's anniversary, host was incredibly kind, and the condo was everything we wanted and more! So close to the beach, and in such an easy to get to location! highly recommend
Guest favourite
Flat in Ocean City
4.97 out of 5 average rating, 59 reviews

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4

MichelleRating, 5 stars2 weeks ago
Kathy and Johns place had an easy check in process. The house is very nice and clean. It was just the right size for the 2 of us. The house is very clean and located mins from the beach. It rained two of the days we were there. We stayed in, the area is very quiet and relaxing. Kathy or John was very responsive if we had any questions. If we go back, I would love to stay here again.
Top guest favourite
Flat in Ocean City
5 out of 5 average rating, 25 reviews

Bayside Bungalow - Waterfront

JoyRating, 5 stars3 weeks ago
Identical to pictures! Beautiful rental in convenient location. The beach and boardwalk were easily walkable and having Fish Tales next door was convenient! My only suggestion would be is to bring an eye mask if you are a light sleeper, there are no shades on kitchen windows so it’s very bright in the early morning since it’s all connected. It helped us to get up and moving in the morning so we didn’t mind. Morgan was quick to reply to messages and a very gracious owner! We will definitely be back.
Guest favourite
Flat in Ocean City
4.86 out of 5 average rating, 111 reviews

Amazing oceanfront view 3 blocks from boardwalk

Jamie ElizabethRating, 5 stars1 month ago
Condo was exactly as described! Amazing oceanfront view! I was also impressed with how much room there was. It was cruiser week so it was a tad bit noisy at night, but other than that and the fact we couldn’t stay longer, we had a wonderful time and enjoyed our stay!
Guest favourite
Flat in Ocean City
4.89 out of 5 average rating, 35 reviews

Endless Summer With Ocean View & Large Deck

DanielleRating, 5 stars2 weeks ago
Laura was a very responsive and wonderful host! She went above and beyond with providing a variety of things to do and see during our stay. She also made sure the check in and check out process went smoothly. The home was well kept, clean and had a great view! Being able to relax on the back porch with the sound of the waves was so peaceful. Our family had a great stay and will definitely be back! Thank you Laura!
Guest favourite
Flat in Ocean City
4.96 out of 5 average rating, 128 reviews

Beautiful Bayfront Condo!

StephanieRating, 5 stars1 week ago
The condo was perfect for our family of 8. It is much larger than the pictures let on. The deck was big enough for all of us to comfortably sit and chat - and Julie has plenty of patio chairs and two tables! Everything was super clean, no clutter, lots of space to spread out and not be on top of each other. The location is perfect too! Quick walk to the beach and some shops. Bus ride can easily take you down to the boardwalk or restaurants you can’t walk to. No need to move your car once you are here. We enjoyed this stay so much we are planning on returning next year. Thank you Julie for sharing your home with us!!
Guest favourite
Flat in Ocean City
5 out of 5 average rating, 38 reviews

SuperHost! Amazing OceanFront View with 2 Pools!

LloydRating, 5 stars2 weeks ago
I was so impressed with Kara’s condo. It was everything I hoped it would be. The decor is very nice and the kitchen is wonderful— modern, spacious, and containing anything you need for cooking or entertaining. The view of the ocean from the 19th floor is both spectacular and calming, whether on the spacious balcony or looking down through the bedroom’s floor to ceiling windows. The building is great. Everyone was friendly and this is a very nice part of Ocean City. Lastly, Kara was terrific. Kind and a great communicator. Plus check in was smooth. If you’re considering a two bedroom, two bathroom condo in this area, I highly recommend this listing!
Guest favourite
Flat in Ocean City
5 out of 5 average rating, 16 reviews

Ocean Front condo with pool

NancyRating, 5 stars2 weeks ago
We arrived the Saturday of Memorial Day Weekend 2025. The directions were specific and spot on. Great parking and easy access. This host went above and beyond to accommodate their guests. Fabulous location! Clean, immaculate and extremely inviting. Balcony was large and truly made you feel like you were on vacation with all the beachy whimsical decor, not too much, just enough! Everything very tastefully equipped. We will be back! Easy access to the beach and the pool, yet private. Thank you. (Crab Stop is the ONLY spot to get your crabs etc, absolutely amazing people!)

Waterfront house rentals

Top guest favourite
Home in Dameron
5 out of 5 average rating, 110 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

MichelleRating, 5 stars3 weeks ago
We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend
Top guest favourite
Home in Reedville
4.95 out of 5 average rating, 241 reviews

Waterfront FamilyFriendly Home Improved for 2023

LoisRating, 5 stars2 weeks ago
Thanks again! We feel at home here. I am noting that holiday weekends are less peaceful in the Northern Neck! We'll remember that. Fondly, Lois and Ken
Guest favourite
Home in Ocean City
4.95 out of 5 average rating, 255 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

ErikaRating, 5 stars3 weeks ago
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!
Guest favourite
Home in Chincoteague
4.9 out of 5 average rating, 113 reviews

Chincoteague Island Creekside Cottage

SherryRating, 5 stars1 month ago
Great spot for a mother/daughters retreat. We enjoyed the cozy and cute decor and each having our own space in the Seaside Cottage. Also, the kitchen was will equipped and we made several meals together as a family. Just a short drive to everything on the island and super close to water and the Misty Pasture. Kathleen was a wonderful host— responsive and proactive throughout our stay. We had a wonderful visit!
Top guest favourite
Home in Chincoteague
4.98 out of 5 average rating, 63 reviews

Saltwater Cowgirls' Cottage

BethRating, 5 stars1 month ago
I chose Chincoteague and the Saltwater Cowgirls' cottage to celebrate a birthday - it was PERFECT. The cottage had character and charm in a nice and quiet neighborhood. The view of the creek was a plus, and we enjoyed watching the families of geese while having coffee on the deck in the mornings. The sunroom was a favorite place for us to chill. The kitchen was well equipped and lacked nothing. We especially loved that our furbabies were welcome - the fully fenced backyard was perfect for our active pups. We absolutely loved the wildlife refuge, the charm of the downtown shops, library and waterfront park. An added bonus - we were within walking distance of the seafood festival! April was very responsive, friendly, and accommodating - We loved staying at the cottage and hope to stay again! It will be the FIRST place we'll check for availability for our next visit to the island.
Top guest favourite
Home in Cambridge
4.99 out of 5 average rating, 171 reviews

Sunset Breezes - quiet waterfront retreat

MicheleRating, 5 stars2 months ago
Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!
Top guest favourite
Home in TYLERTON
4.96 out of 5 average rating, 134 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

SusanRating, 5 stars3 weeks ago
Wonderful accommodations for a relaxing visit to a beautiful island!
Top guest favourite
Home in Onancock
5 out of 5 average rating, 66 reviews

Egret’s Point on the Creek

MichelleRating, 5 starstoday
Everything was AWESOME! Very homey, clean, great location. They had everything and even more than we needed! When we return if we need somewhere to stay and Egrets is available we will definitely book again!

Waterfront apartment rentals

Guest favourite
Apartment in Ocean City
5 out of 5 average rating, 10 reviews

Luxury Waterfront Beach Condo @ Coconut Malorie OC

JessycaRating, 5 stars3 days ago
My husband and I went to celebrate our honeymoon. Suzy & Jerry went above and beyond to make our stay beautiful. Amazing place & hosts. HIGHLY recommend
Superhost
Apartment in Ocean City
4.83 out of 5 average rating, 275 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

PaulRating, 5 stars2 weeks ago
Adam was a great host, answered all questions we had in a timely manner and went above and beyond to check in to make sure we were settling in and enjoying our stay. Our daughter loved the extra amenities of toys and the bunk beds. This home provided beautiful views of the sunrise on the beach and an excellent view of the sunset on the bay. We are already planning our next stay.
Superhost
Apartment in Ocean City
4.88 out of 5 average rating, 196 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

LawrenRating, 5 stars3 weeks ago
Lisa’s place was awesome and exactly how she described it! We loved waking up to the sounds of the ocean and the beautiful views of the bay and ocean. Everything you need is in this condo!!! Thanks again Lisa!!!
Top guest favourite
Apartment in Ocean City
4.99 out of 5 average rating, 96 reviews

The Hideaway By The Bay OCMD

BrendanRating, 5 stars1 day ago
My brother and I came down for the OCMD air show which was unfortunately cancelled but luckily we had this place to stay at! The location was great for the two of us and we easily could have had another person, or two, comfortably. You cannot beat waking up to the bay view! Would definitely recommend or stay again for a return trip. Thanks Corey!
Guest favourite
Apartment in Ocean City
4.97 out of 5 average rating, 126 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

DianeRating, 5 stars3 days ago
My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.
Top guest favourite
Apartment in Ocean City
4.98 out of 5 average rating, 227 reviews

Direct Oceanfront close to Northside Park!

SteveRating, 5 stars1 week ago
Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!
Guest favourite
Apartment in Rehoboth Beach
4.95 out of 5 average rating, 135 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

JasonRating, 5 stars1 week ago
This is my second time staying at this AirbnB and it did not disappoint. The place is super clean, and has an incredible view and location. Key is that if you love the Boardwalk, love the sunrises (5:30 am in the summer), this is the place to be. Perfect for two people who want to cook some meals and be on the balcony facing the ocean, all the time. The hosts are great. Five stars, no equivocation.
Top guest favourite
Apartment in Ocean City
5 out of 5 average rating, 68 reviews

Stylish Beachfront Oasis ~ Ocean Views ~ ♛King Bed

KaylaRating, 5 stars1 week ago
Cozy condo & very clean. Beautiful view. Saw two dolphins! Cocoanuts restaurant is a 2 min walk if you want a quick meal after a long drive arriving. Most restaurants are a short drive 1-5 minutes including the boardwalk. If you Uber they arrived within 1 minute at our condo. Patrick was very responsive as we had a language issue with the TV and he stayed up late to resolve it which was very appreciated. He responded within minutes at a late hour. Elevator access to 5th floor. Very large comfortable bed with good AC. Two beach chairs provided & a fully stocked coffee bar. Comfortable living area. Can beat hearing the waves at night from the balcony. Overall great stay and would stay again!

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