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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, (610 reviews)
"Absolutely adorable, clean and staff super friendly"
United States
Misty
The price is CA $304
CA $341 total
includes taxes & fees
Sep 8 - Sep 9
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (303 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
The price is CA $370
CA $494 total
includes taxes & fees
Aug 13 - Aug 14
Blufin Bungalows & Marina

3. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (139 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is CA $442
CA $745 total
includes taxes & fees
Aug 12 - Aug 13
Pet-friendly creekside cottage w/ backyard

4. Sunset Bay Villas at Chincoteague Island Virginia - direct water front

Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Downtown Chincoteague
9.8 out of 10, Exceptional, (129 reviews)
"Great place with excellent views! Check in was effortless and the condo was one of the cleanest I’ve seen. This was our first time visiting Chincoteague and we will definitely be back!"
United States
Danielle B.
The price is CA $976
CA $1,529 total
includes taxes & fees
Aug 15 - Aug 16
Sunset Bay Villas at Chincoteague Island Virginia - direct water front

5. 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 $355
CA $835 total
includes taxes & fees
Sep 1 - Sep 2
Bayfront Modern Retreat • Dock, Kayaks, Views

6. 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 $307
CA $660 total
includes taxes & fees
Aug 20 - Aug 21
2 Mi to Downtown: Tranquil Abode in Chincoteague!

7. 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)
"Excellent pet friendly location close to the national seashore "
United States
Michael O.
The price is CA $348
CA $624 total
includes taxes & fees
Aug 10 - Aug 11
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

8. 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 $272
CA $542 total
includes taxes & fees
Sep 7 - Sep 8
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

9. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (467 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is CA $112
CA $132 total
includes taxes & fees
Sep 1 - Sep 2
Majestic Hotel & Apartments

10. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (64 reviews)
"Great host, clean space, beautiful water view from the Master, great location right on the water."
United States
Melissa W.
The price is CA $220
CA $628 total
includes taxes & fees
Aug 23 - Aug 24
The purple door at the bay.

11. 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 $314
CA $754 total
includes taxes & fees
Sep 8 - Sep 9
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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, (21 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 $174
CA $358 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Barn Loft: Country Views & Central to Beaches

13. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (6 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 $193
CA $330 total
includes taxes & fees
Sep 9 - Sep 10
Assateague Inn 203 by Seaside Vacations & Sales

14. 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 $195
CA $470 total
includes taxes & fees
Sep 8 - Sep 9
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

15. 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, (51 reviews)
"Great accomodations!"
United States
Linda S.
The price is CA $279
CA $624 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable cottage in gated community, 5 mins to OC and Assateague

16. Spacious 5BR One Level Home Near Ocean City

Spacious 5BR One Level Home Near Ocean City
Berlin
9.0 out of 10, Wonderful, (2 reviews)
"My family loved this rental and I will likely be back. The house was very roomy and the host quickly answered questions. Great for big families. There’s a max capacity of 14 but the house could definitely hold more with ease, and the beds were listed as queens but were all fulls."
United States
Jake S.
The price is CA $433
CA $950 total
includes taxes & fees
Aug 12 - Aug 13
Spacious 5BR One Level Home Near Ocean City

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (39 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 CA $174
CA $411 total
includes taxes & fees
Sep 6 - Sep 7
On Main Street - Apartment C - Berlin, MD

18. 5 Bed/3.5 Bath in Bayside near West Ocean City

5 Bed/3.5 Bath in Bayside near West Ocean City
Bayside
10.0 out of 10, Exceptional, (25 reviews)
"This was our 3rd year of staying here & it really works for our family of 12. It is always clean & well keep & the hosts have been great to work with"
United States
Brent S.
The price is CA $577
CA $1,531 total
includes taxes & fees
Aug 17 - Aug 18
5 Bed/3.5 Bath in Bayside near West Ocean City

19. Balcony w/ Inlet View: Dtwn Ocean City Condo

Balcony w/ Inlet View: Dtwn Ocean City Condo
3.0 star property
Downtown Ocean City
10.0 out of 10, Exceptional, (4 reviews)
"Location was excellent and very clean and spacious"
United States
Paula
The price is CA $464
CA $835 total
includes taxes & fees
Aug 17 - Aug 18
Balcony w/ Inlet View: Dtwn Ocean City Condo

20. 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, (1,315 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 $130
CA $146 total
includes taxes & fees
Sep 7 - Sep 8
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
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.