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Assateague Island Vacation Rentals

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Our top choices for Assateague Island vacation rentals

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (622 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is CA $300
CA $337 total
includes taxes & fees
Sep 15 - Sep 16
Key West Cottages

2. 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 CA $340
CA $611 total
includes taxes & fees
Aug 26 - Aug 27
Pet-friendly creekside cottage w/ backyard

3. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is CA $191
CA $699 total
includes taxes & fees
Aug 31 - Sep 1
Bayfront Modern Retreat • Dock, Kayaks, Views

4. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (361 reviews)
"Great Place, so cute! Our daughter had the best time at the pool, its quiet kids are able to run around and just have a great time! its so relaxing there! Definitely will be coming back!"
United States
Kathryne
The price is CA $116
CA $154 total
includes taxes & fees
Sep 13 - Sep 14
Shore Point Cottages

5. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
The price is CA $218
CA $613 total
includes taxes & fees
Sep 24 - Sep 25
The purple door at the bay.

6. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (488 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is CA $110
CA $130 total
includes taxes & fees
Sep 1 - Sep 2
Majestic Hotel & Apartments

7. 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, (79 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $275
CA $538 total
includes taxes & fees
Sep 22 - Sep 23
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

8. BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (111 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is CA $275
CA $519 total
includes taxes & fees
Sep 23 - Sep 24
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

9. Comfortable cottage in gated community, 5 mins to OC and Assateague

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (53 reviews)
"Convenient amenities at Assateague Point, easy access to Assateague Island and OCMD. Everything in the unit was clean, in proper working order, and we had everything we needed for our family with young children. Would definitely stay here again."
United States
Alexandra
The price is CA $206
CA $519 total
includes taxes & fees
Sep 23 - Sep 24
Comfortable cottage in gated community, 5 mins to OC and Assateague

10. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is CA $202
CA $541 total
includes taxes & fees
Sep 16 - Sep 17
2 Mi to Downtown: Tranquil Abode in Chincoteague!

11. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. I’ve stayed at Assateague Inn on several occasions over the years but this was my first time in 203 and by far the nicest one I’ve stayed in. Newly renovated and tastefully d"
United States
Annette H.
The price is CA $155
CA $283 total
includes taxes & fees
Sep 13 - Sep 14
Assateague Inn 203 by Seaside Vacations & Sales

12. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is CA $186
CA $368 total
includes taxes & fees
Aug 30 - Aug 31
Cozy Barn Loft: Country Views & Central to Beaches

13. 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 CA $227
CA $647 total
includes taxes & fees
Sep 8 - Sep 9
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

14. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (31 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 CA $150
CA $274 total
includes taxes & fees
Sep 14 - Sep 15
Assateageue Inn 104 by Seaside Vacations & Sales

15. OCHG VIRGINIA LEE

OCHG VIRGINIA LEE
2.0 star property
Downtown Ocean City
7.8 out of 10, Good, (9 reviews)
"Love the quaintness of the property. Very clean. Needs updating however did have the old school beach vibe. Really enjoyed our stay. "
United States
Kimberly
The price is CA $234
CA $581 total
includes taxes & fees
Sep 11 - Sep 12
OCHG VIRGINIA LEE

16. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very good, (29 reviews)
"Wonderful views and so big!"
United States
Liz
The price is CA $264
CA $684 total
includes taxes & fees
Sep 7 - Sep 8
Americana Condos 10th street

17. 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, (18 reviews)
"This family friendly home was well appointed and offered the comforts of home. The host thought of everything you might need or want for your vacation. We hope to stay there again soon. The time that was put into getting this home ready for guests was very appreciated. Thank you David and Veronica"
United States
Jennifer
The price is CA $212
CA $625 total
includes taxes & fees
Sep 23 - Sep 24
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

18. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,317 reviews)
"The hotel did not disappoint. The room, the tub and especially the shower was the best. We also loved the view. Would come back again and get the same room. We had the presidential suite."
United States
Nichole
The price is CA $110
CA $123 total
includes taxes & fees
Sep 14 - Sep 15
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

19. Snowbird Bay Cottage | Playground + Community Pool

Snowbird Bay Cottage | Playground + Community Pool
Ocean Pines
9.2 out of 10, Wonderful, (15 reviews)
"nice little place."
United States
Dwayne C.
Snowbird Bay Cottage | Playground + Community Pool

20. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful space. Lots of space for sleeping options. Easy check in process. Close to different shops!"
United States
Virginia D.
The price is CA $193
CA $464 total
includes taxes & fees
Sep 10 - Sep 11
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Assateague Island vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Assateague Island vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Assateague Island vacation rentals we have selected for you start as low as CA $123 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 vacation 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 vacation.

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.