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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, (654 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is CA $276
CA $310 total
includes taxes & fees
Oct 7 - Oct 8
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (334 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is CA $217
CA $324 total
includes taxes & fees
Oct 13 - Oct 14
Blufin Bungalows & Marina

3. 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 $145
CA $487 total
includes taxes & fees
Oct 8 - Oct 9
2 Mi to Downtown: Tranquil Abode in Chincoteague!

4. 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, (1,324 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is CA $135
CA $152 total
includes taxes & fees
Oct 16 - Oct 17
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

5. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (530 reviews)
"Very bice"
United States
Robert
The price is CA $101
CA $121 total
includes taxes & fees
Oct 7 - Oct 8
Majestic Hotel & Apartments

6. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (63 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
The price is CA $101
CA $114 total
includes taxes & fees
Oct 7 - Oct 8
Ocean Terrace Family Apartments

7. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"The staff was very friendly, the apartment was very clean, I love that pets are welcome and the beach and boardwalk are less than 2 minutes walk. EXCELLENT!"
United States
Jennifer
The price is CA $166
CA $300 total
includes taxes & fees
Oct 11 - Oct 12
Wilmington Terrace

8. The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
5.8 out of 10, (59 reviews)
"Not what is lists for, place was very dirty, sheets, sofa, carpets, beds, bathroom. Place smelled like must, humidity and mold. . Do not recommend anyone staying here"
United States
Diego
The price is CA $141
CA $179 total
includes taxes & fees
Oct 11 - Oct 12
The Mallard Apartments

9. Monte Carlo Condos

Monte Carlo Condos
3.0 star property
Downtown Ocean City
7.0 out of 10, Good, (74 reviews)
"Unexpected pet fee on top of resort fees we did expect. Nice and close to boardwalk. Room was quiet, private, spacious."
United States
Ben
The price is CA $143
CA $335 total
includes taxes & fees
Oct 12 - Oct 13
Monte Carlo Condos

10. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.4 out of 10, Very good, (33 reviews)
"Wonderful views and so big!"
United States
Liz
The price is CA $220
CA $645 total
includes taxes & fees
Nov 6 - Nov 7
Americana Condos 10th street

11. Dagsboro Retreat

Dagsboro Retreat
2.0 star property
Dagsboro
10.0 out of 10, Exceptional, (1 review)
"I loved it"
United States
Alexandra
The price is CA $340
CA $340 total
includes taxes & fees
Nov 1 - Nov 2
Dagsboro Retreat

12. Game Room! Waterfront Group Haven in Ocean Pines

Game Room! Waterfront Group Haven in Ocean Pines
3.0 star property
Ocean Pines
The price is CA $649
CA $1,508 total
includes taxes & fees
Oct 18 - Oct 19
Game Room! Waterfront Group Haven in Ocean Pines

13. 2 1/2 Mi to Bethany Boardwalk! Private Retreat!

2 1/2 Mi to Bethany Boardwalk! Private Retreat!
3.0 star property
Ocean View
The price is CA $278
CA $664 total
includes taxes & fees
Oct 11 - Oct 12
2 1/2 Mi to Bethany Boardwalk! Private Retreat!

14. Walk to Maryland Beach: Coastal Condo w/ Balcony

Walk to Maryland Beach: Coastal Condo w/ Balcony
3.5 star property
North Ocean City
The price is CA $302
CA $680 total
includes taxes & fees
Oct 11 - Oct 12
Walk to Maryland Beach: Coastal Condo w/ Balcony
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.