
Waterfront vacation rentals in Assateague Island
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Top-rated waterfront accommodations in Assateague Island
Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.
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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!

Bayfront Ponte Vista ~ 211
Amazing apartment with a fantastic view! Very clean and quiet, will deff come back to stay here again!

Driftwood Condo, 1BRTropical Bayside w/sunsetview
Steven’s place is so cozy, I definitely felt at home. Everything looks so clean and new. Beach access is walkable, and A LOT of options around the area to go walking or driving. I definitely can see me coming back!!! Thanks, Steven, for the wonderful time that I had with my family in OC.

Sunset Haven Downtown
Had a lovely stay. Home is by the river with peaceful views. The New Year celebration was in the park and lots of fun. Kitchen had everything we needed and even some local coffee. Very comfortable bed. Don's Seafood restaurant is next door and food was outstanding. Very short 5 minutes to other shops and restaurants and the Chincoteague Wildlife Refuge. We would stay here 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!
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!

Waterfront & Hot Tub! 4 BR/4 BA - Central Location
I enjoyed staying here for valentines weekend. House is large and very spacious. Only downside was there is limited basics in kitchen to cook with. I would recommend either bringing your own kitchen pans & baking sheets to cook with or just eat out. David was very communicative with questions I had.

Stunning Chesapeake waterfront home
This home was lovely to spend time in and out! I believe the best parts were the screened-in porch, the beautiful kitchen, the backyard by the private dock, the neighborhood kitties, the birds (including water fowl), the nearby walk to quaint Oxford, and much more! Lucas and Heather are fast at responding and enjoyable individuals. You will not be disappointed with this gem of a house! 5 star!

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!

Warwick Farms waterfront Retreat
We would definitely come back here:) The house was so spacious and felt so homey, and the outdoor space and pool was perfect for our family vacation! The kitchen has everything you need to cook yummy meals and we loved that the dining table was big enough to accommodate all 10 of us! The pool was really clean and we had a lot of fun with the diving board:) Also,the views of the river are gorgeous and the guys had fun kayaking and fishing. All in all,,we had a great week!!
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 !:)

Waterfront Condo With Olympic size swimming pool
James was an amazing host. He was responsive, helpful, and kind. The condo was beautiful, clean, and perfect for our family. The neighbors were also very kind and welcoming. My children loved the pool and walking the bay. The views were second to none and the location was perfect since it was minutes away from restaurants, stores, and Bethany beach. We will definitely be booking again!

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!
This wasn't our first time at Stephanie's condo, and it won't be the last! It's clean, comfortable, quiet, and there's plenty of elbow room. Beautiful views right on the beach. Close to some of our favorite places to eat. Stephanie is a great host too!

Water Front Condo w/Pool Short Walk to Beach
This place was great for a little weekend get away. The place has a very homey feel. The location was great, nice and quiet. Brian was extremely responsive and friendly.
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