
Waterfront vacation rentals in Assateague Island
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Top-rated waterfront rentals in Assateague Island
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Popular amenities for Assateague Island waterfront rentals
Waterfront apartment rentals

The Fish House
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!

Bayside Bungalow - Waterfront
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!

Cozy Waterfront Apartment with Pickleball Court
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

Sunset Haven Downtown
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!

3br Waterfront Assateague Island Best View
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!

Amazing oceanfront view 3 blocks from boardwalk
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!

Private Entrance Apartment on the Chesapeake
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!

Dockside Retreat - Waterfront
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

5 BR Waterfront Home - walk to beach
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

Private Beach Getaway at Finest Chesapeake Bay
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.

Waterfront FamilyFriendly Home Improved for 2023
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!

Fresh Air, Waterfront Views, & Pet Friendly
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.

Family & Pet Friendly Private Beach Retreat
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.

Waterfront Vacation Home in Ocean Pines
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.

Spacious Gorgeous Waterfront Home with Sunset View
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.

Enjoy fishing on private dock, kayaks, piano!
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

Entire Downtown Bayfront Condo
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.

Waterfront Condo w/ Balcony, Right on the Canal
Very clean, nice view, host and hostess were quick responders:) a little far from our venue but we would def come back !:)

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

Penthouse condo. Bayside with elevator. Wow Views!
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.

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

UNIQUE Bay Front Sanctuary Condo
Great stay and location. Centralized to everything and everywhere I went.

Direct Oceanfront close to Northside Park!
Clean, comfortable, and convenient! We love this part of Ocean City and Stephanie’s condo did not disappoint.

Blue Haven I Bay I Boatslip I BoardwalkI Inlet
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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