Waterfront vacation rentals in Assateague Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Assateague Island waterfront rentals

Waterfront apartment rentals

Guest favorite
A back porch balcony features two metal swivel chairs and a small round table, overlooking a serene cove. The water is calm, with a grassy shoreline and boats visible in the distance. The surrounding trees provide a natural backdrop.
Apartment in White Stone
4.92 out of 5 average rating, 116 reviews

The Fish House

ScottRating, 5 stars1 month ago
My wife and I have stayed at The Fish House several times. It is a wonderful respite from our urban home life. A great place to relax and appreciate the Northern Neck lifestyle. We love it here!
Top guest favorite
Two comfortable armchairs are positioned near large windows, providing a view of the bay and surrounding homes. A woven pendant light hangs above, while a neutral rug covers the wooden floor. Greenery from a potted plant adds a touch of nature to the space.
Apartment in Ocean City
5 out of 5 average rating, 24 reviews

Bayside Bungalow - Waterfront

GregoryRating, 5 stars7 months ago
Felt super comfortable there. Everything was in walking distance beach, great restaurants bars and we even utilized the kitchen for breakfast and lunch. Loved the coffee set up and the quite seating area on the water out back. We def would recommend and would love to stay again!
Top guest favorite
A cozy seating area features a tufted purple sectional sofa, complemented by textured throw pillows. Natural light filters in through large windows framed by light curtains, illuminating the space. A rustic wooden coffee table adds warmth and character to the room.
Apartment in Cobbs Creek
5 out of 5 average rating, 33 reviews

Cozy Waterfront Apartment with Pickleball Court

BartRating, 5 stars5 months ago
This was our third stay at Clifton, so we and our 2 dogs obviously like staying there. The location is perfect for getting around Matthews as we continue to explore that part of the region. Very nice stay and we look forward to coming back. Bart and Sharon Cameron November 2024
Guest favorite
A blue table is set outdoors with a bottle of red wine and a glass filled with wine beside a plate of chocolates. In the background, a green waterfront park is visible, featuring a pavilion and trees in the distance.
Apartment in Chincoteague
4.86 out of 5 average rating, 179 reviews

Sunset Haven Downtown

RitaRating, 5 stars6 days ago
It was a wonderful experience staying at Carla’s. The location is perfect. It is quite center in town. We loved the little apartment, it has everything we need. We would love to come back again!
Superhost
A serene pool area is depicted, featuring shimmering water reflecting the vibrant sunset. Lounge chairs are positioned along the edge, overlooking the bay. Soft lighting from lanterns creates a welcoming ambiance, while clouds gently drift across the evening sky.
Apartment in Ocean City
4.71 out of 5 average rating, 28 reviews

3br Waterfront Assateague Island Best View

MikeRating, 5 stars9 months ago
Marcia was extremely responsive, on top of any question we had, and provided recommendations for restaurants and other activities. The location was perfect, we could almost walk anywhere we needed to go. The view is amazing and the condo was very clean!
Guest favorite
A dining area features a round wooden table surrounded by four wooden chairs. Large sliding glass doors provide a view of the ocean and open to a spacious balcony. Natural light illuminates the space, enhancing the serene coastal atmosphere.
Apartment in Ocean City
4.86 out of 5 average rating, 107 reviews

Amazing oceanfront view 3 blocks from boardwalk

RebeccaRating, 5 stars2 weeks ago
We had a wonderful time at John‘s condo! The location can’t be beat and it offered everything we needed. We had little issue with the dishwasher and washing machine, but John responded very promptly and took care of everything quick as could be. Highly recommend!
Guest favorite
A stone pathway leads to a wooden deck surrounded by trees. Four outdoor chairs in light colors sit on the deck, accompanied by a planter. Sunlight filters through the branches, creating a serene outdoor space.
Apartment in Exmore
4.87 out of 5 average rating, 179 reviews

Private Entrance Apartment on the Chesapeake

JoshuaRating, 5 stars1 month ago
Erin’s place was the getaway that we definitely needed. We spent our time enjoying the sunsets (stunning pastel colors across the water), watching movies, cooking together, and had a nice meal at a local diner, too (which was recommended in the listing)! The place was so clean, well equipped, and very homey/comfortable. Being situated right on the beach, where in the mornings you can see all of the bay from the windows in the living room and kitchen. Erin was so personable and responsive which we so appreciated. She gave all the information you could need about not just the AirBnB, but the surroundings as well. We felt right at home. They have wonderful neighbors who we met on the beach one of the evenings. Everyone was just so friendly. They were enjoying a beach fire and we talked for a while about how amazing the area is. We have already decided we absolutely will be staying here again! This is the best kept secret quiet beach hideaway! My partner and I LOVED it!
Superhost
A wooden dock extends along the water, lined with multiple posts. Gentle ripples on the surface reflect soft colors from the sunset sky. Buildings are positioned in the background, providing a glimpse of the surrounding environment.
Apartment in Ocean City
4.9 out of 5 average rating, 10 reviews

Dockside Retreat - Waterfront

NatalieRating, 5 stars8 months ago
Great place to stay if you want to be near the nightlife but still private. Everything was perfect and I would 10 out of 10 get back again.

Waterfront house rentals

Guest favorite
An aerial view of a waterfront home showcases the expansive property with lush green landscaping. The house is positioned near a tranquil waterway, surrounded by other residences, emphasizing its peaceful location. The image captures the proximity to the private dock and expansive outdoor spaces.
Home in Bethany Beach
5 out of 5 average rating, 42 reviews

5 BR Waterfront Home - walk to beach

EricRating, 5 stars3 days ago
Joshua was extremely helpful and accommodating, even though I requested to book the day of. Beautiful house, charming neighborhood, nice views, and close to everything! 10/10 recommend
Guest favorite
Aerial view of a spacious property bordered by lush greenery and a sandy beach, showcasing well-maintained lawns. The house features a large outdoor area with views of the water and distant land across the bay, enhancing the serene setting.
Home in Hudgins
5 out of 5 average rating, 17 reviews

Private Beach Getaway at Finest Chesapeake Bay

TashenaRating, 5 stars5 months ago
This home is absolutely beautiful. I loved being able to wake up early and watch the sun rise over the Chesapeake bay. Even though it was cold the kids enjoyed splashing in the water with their rain boots. We spent the Wednesday before Thanksgiving at colonial Williamsburg. Afterwards we ate at Captain George’s, a place Tas recommended. It was absolutely worth it. I was also pleased with being able to make a good Thanksgiving meal. The stay was relaxing and peaceful. We would love to come back in the near future.
Top guest favorite
A light-filled living area features comfortable seating arrangements, including two armchairs and a spacious couch. A dining table is positioned nearby, with views of the water visible through large windows. A patterned area rug adds a pop of color to the hardwood floor.
Home in Reedville
4.95 out of 5 average rating, 237 reviews

Waterfront FamilyFriendly Home Improved for 2023

FrankieRating, 5 stars1 week ago
Had a great time at Karen’s place. My kiddo loved the dock and my wife and I enjoyed kayaking and reading on the porch. Thanks for a nice stay Karen!
Top guest favorite
The exterior of the retreat is showcased, featuring a grassy area leading to a dock with colorful kayaks. A charming blue building with a fish mural is visible, providing access to outdoor amenities. Surrounding trees offer a natural backdrop, enhancing the waterfront setting.
Home in Reedville
5 out of 5 average rating, 55 reviews

Fresh Air, Waterfront Views, & Pet Friendly

HeatherRating, 5 stars6 days ago
We spent a lovely few days at this home and highly recommend it! The location is fantastic -- right on the water on a quiet creek -- with all the things you need to enjoy yourself. We were very happy to have a fully fenced yard since we brought our dogs. If anything, I think the photos undersell the house: for instance, the furniture in the living room is larger and nicer than it appears in the pics, so you can really spread out and relax in there. A note to EV drivers: we brought our EV and there's conveniently an outdoor 110v outlet on the side of the house next to the driveway.
Guest favorite
A spacious two-story house is set against a backdrop of trees, featuring large windows that invite natural light. A wooden deck extends from the home, leading to a sandy beach area visible along the tranquil water's edge.
Home in Heathsville
4.94 out of 5 average rating, 36 reviews

Family & Pet Friendly Private Beach Retreat

JustinRating, 5 stars6 months ago
Responsive and communicative via AirBnb app. Open to small changes we had to make. Beautiful house and wonderful neighborhood. Everything as described and reasonable price. Truly provided the BnB part of AirBnb with linens, cleaning/cooking supplies, and bathroom supplies. Very scenic. The pictures don't do it justice when it comes to the proximity of the dock. It is right outside the window of the master bedroom.
Guest favorite
A tranquil waterfront scene captures a canal-side home surrounded by lush greenery. A private boat slip is visible alongside the property, accommodating boats up to 23' long. The sun-filled exterior features a light-colored facade and a cozy patio, enhancing the serene atmosphere.
Home in Ocean Pines
5 out of 5 average rating, 8 reviews

Waterfront Vacation Home in Ocean Pines

MollyRating, 5 stars6 months ago
Five stars across the board! Great layout with lots of fun space inside and out. We travel with our two rescue dogs and appreciate the owners who welcome them. Great side yard for them to run around off-leash. Ample gates, lights and security in a beautifully decorated home. Second floor deck and sunroom were favorite spots to relax looking out at the water and watching the cute duck family swim the canal. The kitchen is very nice, especially love the fridge! Also a Wine cooler and an extra mini fridge available for those who need them. Was just me and my husband and two dogs; our adult daughter stopped by for two nights and had the whole second floor to herself. Next time, we could easily bring more family members as plenty of room for larger group. After a rough year, we needed the peace and quiet this location brings. Nice neighbors, too.
Guest favorite
An aerial view of a spacious house surrounded by lush greenery and water features. A private pier extends into the water, and vibrant trees frame the property, providing a natural setting. The scene captures the serenity of the landscape and the proximity to the water.
Home in Scotland
4.91 out of 5 average rating, 128 reviews

Spacious Gorgeous Waterfront Home with Sunset View

RonRating, 5 stars1 month ago
This house is perfect for large groups. It is very spacious, with plenty of room to spread out and get comfortable. We enjoyed sitting on the dock taking in the serene natural beauty of the Creek and observing the local birdlife, including Kingfishers, Great Blue Herons, and Bald Eagles. The house is situated very near to the entrance of Lookout Point State Park which we greatly enjoyed exploring on bicycles. Seeing a large wedge of Tundra Swans fly overhead was a special moment. If you want to spend some time relaxing in a beautiful setting in a beautiful and very interesting area with a large group, this house will serve you well.
Superhost
An aerial view captures a spacious landscape featuring a two-story home near the water. The surrounding green lawn includes trees and bushes, and a private dock is visible along the waterfront. Several boats are moored, offering access to nearby waterways.
Home in Kilmarnock
4.94 out of 5 average rating, 16 reviews

Enjoy fishing on private dock, kayaks, piano!

ChristineRating, 5 stars8 months ago
Great spot, beautiful dock, comfortable beds. We had a great time here with dear family friends. Do note you may need to bring neospresso if you’d like to use the machine. Lovely that kayaks and life jackets were included!

Waterfront condo rentals

Guest favorite
A private patio offers water views and features two comfortable black chairs. Sunlight casts shadows on the floor, while a grassy area leads to a nearby dock. The bay's gentle waves can be seen in the background, creating a serene setting.
Condo in Ocean City
4.95 out of 5 average rating, 39 reviews

Entire Downtown Bayfront Condo

HeatherRating, 5 stars8 months ago
This is a great location if you have kids. I love the fact that there was baby gates for the porch and also there was kid friendly cups plates, and utensils. it’s very close to the beach and it’s a very quiet location on the bay. We would definitely stay here again. The house was gorgeous. The beds were very comfortable and very clean. I can’t say not one negative thing about our stay. We would definitely book here again.
Superhost
A serene bedroom space is displayed, featuring a spacious bed with a light brown blanket. A large smart TV is mounted on the wall in front. A decorative sliding barn door and a dresser add to the room's functionality, while light blue walls contribute to a calming ambiance.
Condo in Ocean City
4.88 out of 5 average rating, 51 reviews

Waterfront Condo w/ Balcony, Right on the Canal

AmyRating, 5 stars7 months ago
Very clean, nice view, host and hostess were quick responders:) a little far from our venue but we would def come back !:)
Guest favorite
A spacious outdoor patio features a large dining table with chairs and a relaxed seating area. Overhead string lights add a touch of ambiance. The patio offers views of the wide canal and surrounding buildings, creating a serene outdoor space for guests.
Condo in Ocean City
4.97 out of 5 average rating, 34 reviews

2BR Waterfront | 1st Floor | Patio | Pool | W/D

ShannonRating, 5 stars2 weeks ago
The place was optimum for our mini vacay. We absolutely loved the area, it was peaceful and relaxing and the amenities were just right. Jaqueline remained open and available for communication and was very clear in her expectations of us as guest. Definitely 5 Stars!
Guest favorite
The image shows a view from a private deck overlooking a marina. Several boats are docked along the waterway, adjacent to multifamily buildings with grey rooftops. Natural light brightens the scene, with calm water reflecting the clear sky.
Condo in Ocean City
4.85 out of 5 average rating, 40 reviews

Penthouse condo. Bayside with elevator. Wow Views!

VincentRating, 5 stars7 months ago
This was our 3rd stay at this location. It is the perfect location for us in OC. Having morning coffee on the balcony overlooking the marina is a relaxing way to start the day. Just a few short blocks to the beach and the boardwalk. Having a car in OC is a necessity and the free parking here comes in handy. Looking forward to our next stay.
Guest favorite
A rear deck is shown, overlooking a calm canal. A boat is docked at the pier, with wooden walkways extending along the water. The scene is framed by residential houses in the background, reflecting a peaceful waterfront atmosphere.
Condo in Ocean City
4.85 out of 5 average rating, 101 reviews

1st Floor 3 BR Condo close to Beach with Pool!

KellyRating, 5 stars8 months ago
Mike’s beach house is perfect for a family or group trip. More than enough space to fit everyone and the location is amazing. You’re less than a 5min walk to the beach but also return to a quiet dock rental. It was so calm sitting on the porch each morning looking at the water. Far enough from the hustle and bustle but close enough to enjoy the boardwalk and attractions when wanted. He’s super communicative as well. Would definitely stay again.
Guest favorite
A wooden dock extends along the water, bordered by well-manicured green grass. Dock posts line the edge, and gentle waves can be seen lapping against the surface. A distant boathouse is visible across the bay.
Condo in Ocean City
4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

EdwardRating, 5 stars7 months ago
Great stay and location. Centralized to everything and everywhere I went.
Top guest favorite
An enclosed patio provides a direct view of the ocean, with sandy beach and water visible beyond a railing. Comfortable seating options are arranged with a small table, allowing for relaxation while enjoying the ocean scenery.
Condo in Ocean City
4.98 out of 5 average rating, 222 reviews

Direct Oceanfront close to Northside Park!

HilaryRating, 5 stars6 days ago
Clean, comfortable, and convenient! We love this part of Ocean City and Stephanie’s condo did not disappoint.
Top guest favorite
A well-lit room features two sets of bunk beds with nautical-themed bedding. A cozy seating area with yellow chairs and a small side table is visible. A decorative anchor rug enhances the maritime theme, while soft lighting from wall fixtures adds warmth to the space.
Condo in Ocean City
5 out of 5 average rating, 62 reviews

Blue Haven I Bay I Boatslip I BoardwalkI Inlet

MichelleRating, 5 stars3 days ago
Stayed on a girls trip for the Springfest. We were able to walk to everything. The building and unit are beautiful. The condo was perfect for the 6 of us with each bedroom having its own bathroom. The kitchen had everything we needed and the view from the balcony is great.

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