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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, (620 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 8 - Sep 9
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 $339
CA $609 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 $215
CA $632 total
includes taxes & fees
Aug 25 - Aug 26
Bayfront Modern Retreat • Dock, Kayaks, Views

4. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.2 out of 10, Wonderful, (359 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 $112
CA $148 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, (66 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 $217
CA $609 total
includes taxes & fees
Sep 21 - Sep 22
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, (481 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, (78 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $268
CA $536 total
includes taxes & fees
Sep 19 - Sep 20
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, (110 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is CA $275
CA $527 total
includes taxes & fees
Sep 13 - Sep 14
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 21 - Sep 22
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 $231
CA $572 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, (7 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 $160
CA $287 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 $185
CA $365 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, (47 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $248
CA $664 total
includes taxes & fees
Sep 21 - Sep 22
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 $162
CA $288 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 $256
CA $672 total
includes taxes & fees
Aug 30 - Aug 31
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 $216
CA $630 total
includes taxes & fees
Sep 22 - Sep 23
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.
The price is CA $358
CA $784 total
includes taxes & fees
Aug 25 - Aug 26
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 $467 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Assateague Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.