Holiday Homes in Assateague Island

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Assateague Island

Blufin Bungalows & Marina
Relax in a serene waterfront retreat with enclosed balconies and a tranquil atmosphere.

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (163)
"excellent place to stay on the water"
Blufin Bungalows & Marina
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
Cozy living space with a kitchen featuring a central stove, cabinetry, and a ceiling fan.

Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!

9.6 out of 10, Exceptional, (109)
"Had a great time house was very clean!"
Ocean City Bayside Retreat Unit B - Cozy Family Getaway Near Beach & Dining!
Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.
Enjoy cooking in this well-equipped kitchen with a central island, oven, and ample cabinetry.

Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.

9.8 out of 10, Exceptional, (37)
"Great stay"
Waterfront home, managed privately with lower fees. Close to DE and OC Beaches.
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Relax on the covered balcony with a comfortable sofa and table, taking in the views of the surrounding cityscape.

⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️

9.2 out of 10, Wonderful, (7)
"The location was amazing! Just steps from the beach! The condo was a perfect size for our family which was 5 adults and 2 young kids. It had everything we needed."
⭐️Stunning Renovated Large Balcony 20 Steps to Beach⭐️
Wave Watcher's Condo - Steps to the beach!
Relax in a spacious living area with a sofa and dining table, featuring a washer and dryer.

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (7)
"The place was very clean and very cool, which was nice on the hot days. Some of my party slept on the floor so I'd say it sleeps 10 but overall, wonderful place would recommend to anyone!"
Wave Watcher's Condo - Steps to the beach!
Country Estates getaway near golf & beach with fast WiFi & central AC - dogs OK
Enjoy the serene view from this sunroom with a high ceiling, ceiling fan, and large windows.

Country Estates getaway near golf & beach with fast WiFi & central AC - dogs OK

8.0 out of 10, Very good, (25)
"This property is perfect for a beach weekend It is close enough to go to the beach but far enough away to enjoy the quiet."
Country Estates getaway near golf & beach with fast WiFi & central AC - dogs OK
Congratulations! You have found one of the Best Vacation Homes in Fenwick
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and granite countertop.

Congratulations! You have found one of the Best Vacation Homes in Fenwick

9.8 out of 10, Exceptional, (95)
"The host was terrible. The property is listed as beach front ocean view. It was nothing of that short. The host did not communicate in a timely manner. The grill was disgusting when we got there — unusable. He charged extra money even tho we did not damage any furniture. The front door does not work. Have to use side door that is not convenient. Rooms are terribly small. Our linens arrived late. Stay away. "
Congratulations! You have found one of the Best Vacation Homes in Fenwick
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Enjoy sunbathing and relaxation in a beach area with umbrellas and ocean views.

Bethany Beach and Close by Marinas! Family and Pet Friendly!!

9.2 out of 10, Wonderful, (76)
"Stayed with friends, great location. Comfortable!"
The price is NZ$654
includes taxes & fees
8 Sept - 9 Sept
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Sunset Island is Loved for it's Amazing Amenities
Relax by the pool surrounded by lounge chairs and umbrellas, with a gazebo and ocean views.

Sunset Island is Loved for it's Amazing Amenities

Sunset Island is Loved for it's Amazing Amenities
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
Relax in a comfortable living room with a sofa, armchair, and fireplace.

Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

10.0 out of 10, Exceptional, (142)
"Perfect cozy place to stay at the end of a quiet pine tree lined street with easy access to the national park and all it offers."
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
Fabulous Fenwick Island Waterfront property!
Enjoy a peaceful meal or relaxation on the deck overlooking the calm water.

Fabulous Fenwick Island Waterfront property!

10.0 out of 10, Exceptional, (202)
"Great place! Lots of kid friendly toys, fully equipped kitchen. Backyard was excellent! "
Fabulous Fenwick Island Waterfront property!
Bayfront cottage offers amazing views of the water and Assateague Island
Enjoy a serene view of the open field and water from this patio, featuring a comfortable seating area with a table and umbrella.

Bayfront cottage offers amazing views of the water and Assateague Island

9.6 out of 10, Exceptional, (40)
"Wonderful stay! Very clean and relaxing!"
Bayfront cottage offers amazing views of the water and Assateague Island
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Fridge, microwave, oven, stovetop

Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes

8.8 out of 10, Excellent, (3)
"property was very clean, lot of space everything was equipped in kitchen for cooking. plus kids toys. We had a great time staying that the property."
Beautiful Home in Ocean Pines with Water Access for SUP's and Canoes
Bethany Beach New Castle 4BR 2BA Canal Front Home
TV, offices

Bethany Beach New Castle 4BR 2BA Canal Front Home

9.4 out of 10, Exceptional, (3)
"The beach house was so cute and short distance from the beach. It had everything we needed ! The hosts were very nice and ready to help "
Bethany Beach New Castle 4BR 2BA Canal Front Home
Clearwater home - Elevated dog-friendly retreat with a deck plus pool & tennis
Relax on the deck with a view of the surrounding trees, featuring a comfortable seating area and a small ladder.

Clearwater home - Elevated dog-friendly retreat with a deck plus pool & tennis

9.0 out of 10, Wonderful, (11)
"We enjoyed the house and its location. Usually we rent beachfront, but for this offseason visit, this house served us well. We enjoyed sitting on the back deck and enjoyed the quite nature sounds. The neighborhood was very quiet in the offseason."
The price is NZ$1,069
includes taxes & fees
19 Aug - 20 Aug
Clearwater home - Elevated dog-friendly retreat with a deck plus pool & tennis
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Enjoy ocean views from the covered porch, where you can relax in Adirondack chairs or dine al fresco.

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

9.6 out of 10, Exceptional, (15)
"We stayed three nights and they were all delightful. The cabins are super clean, well equipped, comfortable beds, screened in front porch.- in other words anything you could wish! My only critique is that I don’t think the smoke alarm in the CO2 detectors were listed in the ad and they should be because they definitely are there!We will gladly come again someday."
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Serene Family Home with Heated Pool 30 Steps from Beach
Relax on the outdoor deck, surrounded by a swimming pool and a two-story building with a balcony.

Serene Family Home with Heated Pool 30 Steps from Beach

9.8 out of 10, Exceptional, (19)
"Very nice home in a perfect location loved pool and access to ocean"
Serene Family Home with Heated Pool 30 Steps from Beach
Steps to Shore: Spacious Bethany Beach Retreat
Enjoy meals with a view of the beach from this dining area featuring a large window, dining table, and chandelier.

Steps to Shore: Spacious Bethany Beach Retreat

10.0 out of 10, Exceptional, (1)
"The house is located steps from the beach and the host provides the beach toys, towels, and most of what you need. Our family enjoyed our stay and it’s perfect for kids too.When we ran into some issues the host took care of it right away. We will be back. "
Steps to Shore: Spacious Bethany Beach Retreat
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Outdoor dining

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

The price is NZ$4,508
includes taxes & fees
24 Aug - 25 Aug
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
Water front, open bay views from both decks!!
Enjoy a serene view of the lake from the comfort of this room, featuring a large window and a spacious deck with a bench.

Water front, open bay views from both decks!!

10.0 out of 10, Exceptional, (70)
"Great place to stay!"
Water front, open bay views from both decks!!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Assateague Island Hotel Reviews

Quality Inn Ocean City Beachfront

Quality Inn Ocean City Beachfront

10/10 Excellent
"I think that average good. "
Mohammad 1-night trip
Posted 1 day ago
Quality Inn Ocean City Beachfront