
Waterfront vacation rentals in Assateague Island
Find and book unique waterfront accommodations on Airbnb
Top-rated waterfront accommodations in Assateague Island
Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Assateague Island waterfront rentals
Waterfront apartment rentals

Luxury Waterfront Beach Condo @ Coconut Malorie OC
The place is very nice and location is in walking distance of many nice restaurants. Suzy was very response and we were able to check in early. Thank you

The Pelican of Bahia Vista 3B/2b
Outstanding communication and the stay was 100% as described. Beautiful place and the sites were amazing. I highly recommend Violet and her property! So very welcoming and clean! Just a short walk to the boardwalk and night life, then to be able to come back to have peace and quietness was so satisfying. Don’t hesitate to book this property! It’s a must!!

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4
We were looking for a Labor Day weekend getaway and stumbled upon this listing. We loved how close we were to an assortment of shops and even did some morning walks to Starbucks. We personally prefer the beaches farther away from the boardwalk so this was a perfect location for us! The hosts were amazing and answered us so quickly but also provided us with check in/ check out information before we even needed to ask. We had a wonderful time and would be back!

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!

Driftwood Condo, 1BRTropical Bayside w/sunsetview
This was our second stay at Driftwood condo, approximately one year later. The condo is just as wonderful as we remember - adorable furnishings and cleaner than any hotel I’ve ever stayed. Very comfortable accommodations, beds, linens etc. Easy to access and had everything we needed for a great stay. Thank you!

Sunset Haven Downtown
The apartment was very cozy. The hosts were helpful and responsive and provided a lots of local recommendations. Would love to stay there 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
Great spot! Right in the beach and super close to the boardwalk. It was clean but not super clean. We were really happy, the condo came with more than we expected. It also was bigger than we expected. We had a wonderful time! We would definitely stay here again. I was pleasantly surprised with the amount of kitchen items! I was expecting much less. 5/5 for a beachfront condo that is affordable!
Waterfront house rentals

Waterfront Getaway with Dock
I’ve enjoyed Trevor’s place each for the past few years. He’s a great host! Very responsive. Great communications. Always a pleasure!

Charming Waterfront Cottage w/2 King Suites + Dock
This is our third stay at Jennifer’s home, and wow, another 5 star stay. Woke up to 2025 and a placid bay view, great coffee, and a perfect night’s sleep! Gold star amenities, luxe beds, and insider tips on the places to go and eat. Book with confidence. 10 min from the ocean, ultra luxe accommodations.

Newly Renovated Modern 3 bed 2 bath Water Front
The Riverhouse exceeded our expectations and deserved the 5 or more rating! The place was immaculate, had a gorgeous river view, and the hosts were extremely accommodating and responsive! Highly recommended!

Bayside House at Vaux Hall Farm
Perfect location while attending an event at Vaux Hall. Would be great if boating on the Chesapeake as well. Plenty of dock space!

Waterfront & Hot Tub! 4 BR/4 BA - Central Location
We stayed at David’s house over a weekend with a few buddies and we had a great stay. The house was clean and well taken care of, and David was super helpful and quick to respond. He even reached out to me beforehand to offer an early check in if that worked better for our arrival time. We really enjoyed the amazing backyard and the hot tub was such a nice touch. I would certainly recommend to a friend!

Stunning Chesapeake waterfront home
Lucas was a fantastic host! From our first communication until our check out, Lucas made so many accommodations to help make our stay the best ever. Being the host of an Airbnb myself, I understand what makes guests stay memorable!! Lucas went the extra mile. My family was here from all over the country for my father’s funeral. Lucas offered a late check out after the funeral. This was so thoughtful and kind. The waterfront views and proximity to downtown Oxford was fantastic. The screened in porch was ideal for my family to congregate and talk around the outside fire. I cannot say enough about this home. We can’t wait to come back soon!

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach
We had the most amazing stay at Donna’s house! The place was spotless, super cozy, and so stylish, with plenty of room for everyone to kick back and relax. The quiet neighborhood made it the perfect spot to unwind and recharge. We absolutely loved hanging out on the outdoor decks, soaking up the views, and enjoying our morning coffee while watching the gorgeous sunrises over the canal. The screened porch was perfect for unwinding and catching the sunset. The beach was only a short distance away, and the kayaks and SUPs were such a fun way to explore the bay. Donna was an incredible host—always responsive and so helpful throughout our stay. We seriously can’t recommend her beach house enough!

Beautiful Waterfront Home-Private, Clean, Relaxing
Such beautiful and cozy house with a great view of the lake. It was absolutely spotless and just as described in the listing. The host was very kind and always responsive. I would definitely stay again when I return to visit the area. Highly recommend!
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 !:)

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!
Great view from the living room and the bedroom!! Loved the location!!! Close the Bethany and to the OC boardwalk. Great communicator too!! I Love this place and will definitely be back!!!

Blue Haven I Bay I Boatslip I BoardwalkI Inlet
We stayed at Julie’s place during Oceans Calling this year and have to say that it was a great location. Condo was beautiful and Julie took care of some of the dumb things you don’t think about like conveniently placed outlets and labeling things like switches for lights. There’s also a luggage cart and elevator to get your stuff to and from the condo which we weren’t expecting. Condo is spacious and didn’t feel cramped at all. All the three bathrooms can be accessed directly from a bedroom so that’s great too. View is fantastic and the location is very walkable to surrounding areas. We also found some street (non pay) parking around the adjacent streets near the oldest bar in OC which saved us some headaches for extra cars. Julie is a very responsive and thorough host. Overall very happy with this booking.

Water Front Condo w/Pool Short Walk to Beach
Brian's place is such an excellent condo to stay in Ocean City. Quiet and beautiful inside, easy to walk to the beach and nearby restaurants outside. This was a great place for me and my family to stay. The canal is quite nice to see while drinking morning coffee, and the place was just immaculate. Really enjoyed our time here. Highly recommend this place for a comfortable beach getaway!
Destinations to explore
- Fitness-friendly rentals Assateague Island
- Rentals with pools Assateague Island
- Rentals with a firepit Assateague Island
- Rentals with a patio Assateague Island
- Pet-friendly rentals Assateague Island
- Family-friendly rentals Assateague Island
- Rentals with a kayak Assateague Island
- Rentals with a washer and dryer Assateague Island
- Condo rentals Assateague Island
- Cottage rentals Assateague Island
- Beachfront rentals Assateague Island
- Rentals with outdoor seating Assateague Island
- Townhouse rentals Assateague Island
- House rentals Assateague Island
- Rentals with beach access Assateague Island
- Kid-friendly rentals Assateague Island
- Rentals with a fireplace Assateague Island
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom