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Assateague Island Holiday Rentals

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Holiday Rentals in Assateague Island

Cottage in Downtown Chincoteague

3.0 star property
9.8 out of 10, Exceptional, (486)
"We love Key West Cottages!"
United States
Jonathan
Key West Cottages

Aparthotel in Midtown Ocean City

3.0 star property
7.4 out of 10, Good, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
The price is NZ$168
includes taxes & fees
7 Jan - 8 Jan 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Aparthotel in Downtown Ocean City

2.5 star property
6.2 out of 10, (350)
"Clean and very friendly staff"
United States
Randy
Majestic Hotel & Apartments

Apartment in North Ocean City

3.0 star property
9.2 out of 10, Wonderful, (133)
"Our room was very clean and the ocean view was breathtaking. "
United States
Kelly
Saint Tropez

Apartment in North Ocean City

3.5 star property
8.6 out of 10, Excellent, (58)
"Property was in a great location. Check in and check out was easy. Having a hot tub and deck with table and chairs was nice. Unit was clean with an exception of the floors. I can understand it being a little sandy because of being at the beach, but there were tortilla chips in several areas of the floor. "
United States
Tami
Club Ocean Villas II by Coolvacay

Cottage in Berlin

3.0 star property
9.4 out of 10, Exceptional, (300)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages

Condo in Downtown Ocean City

3.5 star property
8.4 out of 10, Very good, (19)
"straight fire, definitely going back"
United States
stephen
The price is NZ$809
includes taxes & fees
13 Dec - 14 Dec
Americana Condos 10th street

Condo in Downtown Ocean City

3.0 star property
6.8 out of 10, (58)
"The condo was small, but it’s still accommodated my family of eight and we were right next to the pool, which was great for the kids anytime we needed something. We just called the Hotel and it was brought over in a reasonable amount of time or we could pick it up later. Staff were very friendly."
United States
Amy
Monte Carlo Condos

Condo resort in Midtown Ocean City

3.0 star property
8.4 out of 10, Very good, (39)
"One of the cleanest places I’ve stay at loved it ! "
United States
Kelsey
Bay Club Resort by Coolvacay

Aparthotel in Downtown Ocean City

3.0 star property
7.4 out of 10, Good, (170)
"Close to boardwalk, beach, shopping and dining. Also it was very affordable."
United States
ANGELA
Boardwalk One

Condo in Downtown Ocean City

9.8 out of 10, Exceptional, (62)
"The condo was very convenient to get to the beach. Beautiful view of the bay. Plenty of room for everyone to enjoy the stay. "
United States
David H.
The price is NZ$611
includes taxes & fees
14 Dec - 15 Dec
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (134)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is NZ$532
includes taxes & fees
9 Dec - 10 Dec
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Holiday Home in Down the Marsh

3.0 star property
9.6 out of 10, Exceptional, (207)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (142)
"We had great time. The house was clean and perfect for my entire family. I would recommend and go back. "
United States
Kristina P.
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Apartment in Downtown Ocean City

3.0 star property
9.2 out of 10, Wonderful, (5)
"Everything around was excelente, only bad things wasn’t clean and need some updates, everything else was really nice. The hostess was friendly and helpful. "
United States
Anonymous traveller
ELIS APARTMENT

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (120)
"Great property in a great location. Host was quick to get ahold of and the instructions were incredibly easy. Highly recommend this property for a family or large group. We would stay here again!"
United States
Joseph G.
The price is NZ$523
includes taxes & fees
9 Dec - 10 Dec
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

Holiday Home in North Ocean City

9.8 out of 10, Exceptional, (11)
"Beautiful home. Our family of 13 were very comfortable and really enjoyed our stay. Only negative was no furniture on the deck. The pictures showed a table and chairs along with couches and comfy chairs. We had to bring out beach chairs to sit. Loved the big side yard and fire pit. "
United States
Peggy K.
⭐️Brand New High End Luxury Bayside Mansion Pool⭐️

Holiday Home in Midtown Ocean City

8.2 out of 10, Very good, (55)
"The property was steps away from the beach, so it was easy to walk to and back from the beach. The size was amazing, we had a large group and everybody was able to sleep comfortably. The kitchen was also a good size and there were many bathrooms. However it was not clean. There were items from previous visitors found, sometimes food crumbs, and sand. It’s great for people who need a big space but not for those who want an absolute clean environment."
United States
Julio C.
Ocean Block End Unit Townhome 300ft Feet From Beach W/ Ocean View

Condo in Downtown Ocean City

9.6 out of 10, Exceptional, (49)
"Overall a very nice property. Great location with many food and activity options within walking distance."
United States
Erik G.
SunburstParadise: LUX TH OceanView DOWNTOWN BOARDWALK 3BR 3BA with 2 Car Garage

Holiday Home in Selbyville

2.0 out of 10, (1)
"Property owner, claims VRBO booked property without his knowledge. So it ended up being double booked. He made us pay 500 additional to stay. Although he did allow us to stay an additional night. Its the principal. The kitchen was full of ants. He had someone come and put ant traps down but that still didn't help. Non of the beds had sheets on them. I have never rented a house that doesn't have clean linen on the beds when you get there. Definitely do not recommend. "
United States
Jeneal M.
Waterfront amazing 3 bedroom house
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.
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Top Assateague Island Hotel Reviews

Find out more about Assateague Island

Everything you need to know about Assateague Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Assateague Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Assateague Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Assateague Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Assateague Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Assateague Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Assateague Island holiday rentals we have selected for you start as low as NZ$168 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Assateague Island rentals

At Expedia, we put the best Assateague Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Assateague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Assateague Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Assateague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.