Assateague Island Holiday Rentals

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Our top choices for Assateague Island holiday rentals

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (511 reviews)
"This was a Wonderful place to stay!! So much charm a the staff was wonderful! "
United States
CHRISTIE
Key West Cottages
9.8 out of 10, Exceptional, (39 reviews)
"Loved this property! Owners were very responsive! "
United States
Michelle K.
The price is NZ$525
includes taxes & fees
15 Mar - 16 Mar
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
9.8 out of 10, Exceptional, (43 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
The price is NZ$525
includes taxes & fees
24 Mar - 25 Mar
Comfortable cottage in gated community, 5 mins to OC and Assateague

Cottage in Berlin

Shore Point Cottages
3.0 star property
9.4 out of 10, Exceptional, (304 reviews)
"The location of shore point cottages is a pleasant and peaceful one. It's far enough out of the hustle and bustle of the boardwalk area. Yet close enough to everything that makes Ocean City a fun place to visit. Definitely a place to come back to and stay again."
United States
Mike
Shore Point Cottages
9.2 out of 10, Wonderful, (79 reviews)
"The house and property was very spacious and comfortable. We enjoyed our stay and visit to the area very much."
United States
gisela j.
The price is NZ$607
includes taxes & fees
26 Mar - 27 Mar
Bethany Beach and Close by Marinas! Family and Pet Friendly!!
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is NZ$479
includes taxes & fees
2 Mar - 3 Mar
Cozy cottage w/ creekside fire pit & pet‑friendly
10.0 out of 10, Exceptional, (32 reviews)
"Great location, place very clean and perfect for our trip!"
United States
Ed S.
The price is NZ$545
includes taxes & fees
1 Mar - 2 Mar
Charming 2-Bed Condo Steps From the Beach!

Apartment in Downtown Berlin

On Main Street - Apartment C - Berlin, MD
9.2 out of 10, Wonderful, (29 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is NZ$383
includes taxes & fees
2 Mar - 3 Mar
On Main Street - Apartment C - Berlin, MD
9.8 out of 10, Exceptional, (16 reviews)
"Walkable to the beach so you didn’t need to wait for the tram if you didn’t want to, second floor which is great, "
United States
Marianne B.
Sea Colony condo with pools, hot tub, tennis, gym, & private deck
10.0 out of 10, Exceptional, (11 reviews)
"Was all around great experience with great and accommodating hosts."
United States
Garrett B.
The price is NZ$325
includes taxes & fees
1 Mar - 2 Mar
Ocean! Ocean! Ocean! 🏖 Beautiful Condo!!
9.0 out of 10, Wonderful, (35 reviews)
"Perfect place to stay for oceans calling! On bus route but not in the craziness of the direct festival area."
United States
Jennifer F.
The price is NZ$344
includes taxes & fees
2 Mar - 3 Mar
Ocean calling & country concert availability!
9.6 out of 10, Exceptional, (22 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is NZ$315
includes taxes & fees
2 Mar - 3 Mar
Assateague Inn 104 by Seaside Vacations & Sales
8.4 out of 10, Very good, (29 reviews)
"Great condo, very clean, would stay here in the future."
United States
Carla B.
Bethany Bay Getaway w/ Free WiFi, Shared Pool, & Sports Courts
9.8 out of 10, Exceptional, (61 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
The price is NZ$732
includes taxes & fees
1 Mar - 2 Mar
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
10.0 out of 10, Exceptional, (18 reviews)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is NZ$374
includes taxes & fees
1 Mar - 2 Mar
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
9.6 out of 10, Exceptional, (93 reviews)
"Good location with great views."
United States
Mark M.
The price is NZ$793
includes taxes & fees
1 Mar - 2 Mar
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
9.8 out of 10, Exceptional, (246 reviews)
"Great location and clean!"
United States
Susan V.
The price is NZ$372
includes taxes & fees
26 Mar - 27 Mar
Ocean City Maryland Condo, ocean side 50 steps to the beach! On 7 40th Street
10.0 out of 10, Exceptional, (66 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is NZ$450
includes taxes & fees
1 Mar - 2 Mar
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
10.0 out of 10, Exceptional, (40 reviews)
"Absolutely wonderful place very nice owner"
United States
Joseph N.
The price is NZ$388
includes taxes & fees
1 Mar - 2 Mar
Fantastic Bay View with romantic sunsets!

Holiday Home in Captain's Cove

The purple door at the bay.
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is NZ$733
includes taxes & fees
1 Mar - 2 Mar
The purple door at the bay.
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$163 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.