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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, (665 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $268
CA $301 total
includes taxes & fees
Nov 25 - Nov 26
Key West Cottages

2. 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, (1,331 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 $146
CA $163 total
includes taxes & fees
Oct 26 - Oct 27
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

3. Americana Condos 10th street

Americana Condos 10th street
3.5 star property
Downtown Ocean City
8.6 out of 10, Excellent, (34 reviews)
"Wonderful views and so big!"
United States
Liz
The price is CA $223
CA $642 total
includes taxes & fees
Oct 30 - Oct 31
Americana Condos 10th street

4. 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 $128
CA $346 total
includes taxes & fees
Oct 29 - Oct 30
Monte Carlo Condos

5. 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 $420
CA $1,238 total
includes taxes & fees
Nov 8 - Nov 9
Game Room! Waterfront Group Haven in Ocean Pines

6. The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
5.6 out of 10, (60 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 $700
CA $805 total
includes taxes & fees
Oct 26 - Oct 27
The Mallard Apartments

7. 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 $334
CA $334 total
includes taxes & fees
Nov 1 - Nov 2
Dagsboro Retreat

8. Luxury Home 3 Mi to Bethany Beach Boardwalk!

Luxury Home 3 Mi to Bethany Beach Boardwalk!
3.0 star property
Ocean View
The price is CA $253
CA $1,113 total
includes taxes & fees
Oct 31 - Nov 1
Luxury Home 3 Mi to Bethany Beach Boardwalk!

9. 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 $322
CA $705 total
includes taxes & fees
Oct 26 - Oct 27
2 1/2 Mi to Bethany Boardwalk! Private Retreat!

10. 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 $297
CA $668 total
includes taxes & fees
Oct 26 - Oct 27
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.