A beach with gentle waves and a clear sky.

Assateague Island Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Assateague Island holiday rentals

A waterfront house with a balcony, dock, and a view of the water.

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (658 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is NZ$389
includes taxes & fees
15 Oct - 16 Oct
Key West Cottages
Exterior

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (338 reviews)
"It was so fun to be sleeping right on the water."
United States
Marissa
Blufin Bungalows & Marina
A covered porch with wicker chairs and a view of the outdoors.

3. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
The price is NZ$574
includes taxes & fees
27 Oct - 28 Oct
Pet-friendly creekside cottage w/ backyard
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

4. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is NZ$357
includes taxes & fees
18 Oct - 19 Oct
Assateageue Inn 104 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

5. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"We had a mommy-daughter mini-getaway to celebrate her 9th birthday! The area is very walkable, but also easy to drive and navigate the rest of the island. Our room was clean, as advertised, and the perfect place to relax, eat, and recharge. We loved the pool! The check-in/check-out process was very easy."
United States
Nora T.
The price is NZ$380
includes taxes & fees
18 Oct - 19 Oct
Assateague Inn 203 by Seaside Vacations & Sales
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

6. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (71 reviews)
"Overall nice stay!"
United States
Becky S.
The price is NZ$847
includes taxes & fees
9 Nov - 10 Nov
Bayfront Modern Retreat • Dock, Kayaks, Views
A sandy beach with footprints and a person walking.

7. Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is NZ$706
includes taxes & fees
16 Oct - 17 Oct
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

8. Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (10 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is NZ$498
includes taxes & fees
20 Oct - 21 Oct
Central Location~Walk 2 Dining! Beach Pass & Gear!
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

9. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
9.8 out of 10, Exceptional, (19 reviews)
"Great location, easy check in, very clean, well decorated"
United States
sue g.
The price is NZ$560
includes taxes & fees
26 Oct - 27 Oct
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A sunroom with wicker furniture, large windows, and a view of the water.

10. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Great location"
United States
Rick K.
The price is NZ$797
includes taxes & fees
20 Oct - 21 Oct
The purple door at the bay.
A beach with waves and a sunset.

11. Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (83 reviews)
"Great location, great spaces, the hosts thought of everything!Table was perfect for plenty of puzzle sessions. Bookstores, thrift shops, coffee shops, Island creamery, fishing, trolley, everything was so convenient.Thanks!Maggie"
United States
Margaret B.
The price is NZ$583
includes taxes & fees
9 Nov - 10 Nov
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
A two-story building with a central entrance and a wooden walkway leading to it.

12. Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Lauren P.
The price is NZ$358
includes taxes & fees
22 Oct - 23 Oct
Assateague Inn 213 by Seaside Vacations & Sales
A living room with a blue sofa, a wooden dining table with chairs, a TV, and a balcony with blue curtains.

13. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (9 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
The price is NZ$358
includes taxes & fees
18 Oct - 19 Oct
Assateague Inn 106 by Seaside Vacations & Sales
A house surrounded by dense trees and a wooden dock extending into a body of water.

14. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful, clean, well appointed house in a peaceful setting. Easy & quick (20 minute) access to Assateague & Ocean City beaches without the chaos of staying in OC. Berlin and Snow Hill are fun historic eastern shore towns to explore. Take a day trip south to Pokomoke State Park for a calming non-beach nature experience. So nice we booked it again on our first day there."
United States
David M.
The price is NZ$803
includes taxes & fees
3 Nov - 4 Nov
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A two-story building with a central entrance and a wooden walkway leading to it.

15. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (37 reviews)
"The location was central with a deck out on the marsh, which was lovely. The pool seemed well kept and was nice. It was clean and the communication with the hosts was quite good. The smart TVs didn’t really work and could only work with live tv. No apps worked. Overall, though, would stay again."
United States
Erin
The price is NZ$360
includes taxes & fees
19 Oct - 20 Oct
Assateague Inn 111 by Seaside Vacations & Sales
A living room with a sofa, ottoman, and dining table with chairs. There is a television on the wall and a window with a view of the outside.

16. Assateague Inn 110 by Seaside Vacations & Sales

Assateague Inn 110 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (12 reviews)
"The whole stay was excellent and the property was in an excellent location. Surprisingly quiet considering the proximity to restaurants and activities."
United States
Anonymous traveller
The price is NZ$401
includes taxes & fees
18 Oct - 19 Oct
Assateague Inn 110 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

17. Assateague Inn 100 by Seaside Vacations & Sales

Assateague Inn 100 by Seaside Vacations & Sales
Chincoteague
8.6 out of 10, Excellent, (13 reviews)
"Quiet area and close to all attractions. Very fast response with any questions before and during stay. Would recommend!"
United States
Sue S.
The price is NZ$357
includes taxes & fees
19 Oct - 20 Oct
Assateague Inn 100 by Seaside Vacations & Sales
A multi-story building with a white exterior, balconies, and a sign indicating it is an apartment complex.

18. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (67 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is NZ$114
includes taxes & fees
15 Oct - 16 Oct
Ocean Terrace Family Apartments
A beachside boardwalk with shops, a Ferris wheel, and a tram.

19. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
The price is NZ$409
includes taxes & fees
18 Oct - 19 Oct
On Main Street - Apartment C - Berlin, MD
A covered patio with a table and chairs, overlooking a beach.

20. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (531 reviews)
"Right in front of the board walk and almost center to everything"
United States
Wilber
The price is NZ$137
includes taxes & fees
26 Oct - 27 Oct
Majestic Hotel & Apartments
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

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

10/10 Excellent
"The staff was super friendly and greeted as we came to the top of the steps from the counter. The property was beautiful, room was very clean and spacious. Will definitely be staying there for future visits to OCMD."
Jessica 3-night trip
Posted 6 hours ago
Holiday Inn & Suites Ocean City by IHG

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$114 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.