Assateague Island Vacation Rentals

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Our top choices for Assateague Island vacation rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (507 reviews)
"Love the resort! "
United States
Hannah
Key West Cottages

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,300 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is CA $105
CA $134 total
includes taxes & fees
Mar 10 - Mar 11
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (303 reviews)
"The location of shore point cottages is a pleasant and peaceful one. It's far enough out of the hustle and bustle of the boardwalk area. Yet close enough to everything that makes Ocean City a fun place to visit. Definitely a place to come back to and stay again."
United States
Mike
Shore Point Cottages

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, (43 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
The price is CA $137
CA $433 total
includes taxes & fees
Feb 15 - Feb 16
Comfortable cottage in gated community, 5 mins to OC and Assateague

Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools
Selbyville
9.8 out of 10, Exceptional, (39 reviews)
"Loved this property! Owners were very responsive! "
United States
Michelle K.
Mallard Lakes Waterfront Beach Condo in Fenwick Island with Two Pools

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (29 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is CA $98
CA $316 total
includes taxes & fees
Feb 9 - Feb 10
On Main Street - Apartment C - Berlin, MD

Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Ocean View
9.2 out of 10, Wonderful, (79 reviews)
"The house and property was very spacious and comfortable. We enjoyed our stay and visit to the area very much."
United States
gisela j.
The price is CA $103
CA $508 total
includes taxes & fees
Feb 9 - Feb 10
Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Cozy cottage w/creekside fire pit & pet‑friendly

Cozy cottage w/creekside fire pit & pet‑friendly
Up the Neck
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is CA $186
CA $398 total
includes taxes & fees
Feb 11 - Feb 12
Cozy cottage w/creekside fire pit & pet‑friendly

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (209 reviews)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
9.8 out of 10, Exceptional, (62 reviews)
"Great location walking distance to everything. Thank you so much for a great stay."
United States
valerie0472
The price is CA $62
CA $479 total
includes taxes & fees
Feb 9 - Feb 10
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (61 reviews)
"This is a unique home with beautiful views! The amenities were wonderful, the home was so clean, and Nick was great with checking in to make sure everything was good. Would definitely stay here again! "
United States
Kristy C.
The price is CA $98
CA $596 total
includes taxes & fees
Feb 9 - Feb 10
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Quiet street in midtown that is close enough to walk to restaurants & shopping.

Quiet street in midtown that is close enough to walk to restaurants & shopping.
North Ocean City
10.0 out of 10, Exceptional, (14 reviews)
"Nicely decorated and fully equipped. Great location … within walking distance of anything you could need. "
United States
Joan C.
The price is CA $154
CA $388 total
includes taxes & fees
Feb 9 - Feb 10
Quiet street in midtown that is close enough to walk to restaurants & shopping.

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (25 reviews)
"Loved that it was right on the bay. "
United States
Debra
The price is CA $163
CA $213 total
includes taxes & fees
Feb 12 - Feb 13
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
North Ocean City
10.0 out of 10, Exceptional, (18 reviews)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is CA $101
CA $308 total
includes taxes & fees
Feb 9 - Feb 10
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (22 reviews)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveller
The price is CA $138
CA $259 total
includes taxes & fees
Feb 9 - Feb 10
Assateague Inn 104 by Seaside Vacations & Sales

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"Perfect place to stay for oceans calling! On bus route but not in the craziness of the direct festival area."
United States
Jennifer F.
The price is CA $86
CA $283 total
includes taxes & fees
Feb 9 - Feb 10
Ocean calling & country concert availability!

Fantastic Bay View with romantic sunsets!

Fantastic Bay View with romantic sunsets!
Midtown Ocean City
10.0 out of 10, Exceptional, (40 reviews)
"Absolutely wonderful place very nice owner"
United States
Joseph N.
The price is CA $164
CA $322 total
includes taxes & fees
Feb 9 - Feb 10
Fantastic Bay View with romantic sunsets!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Deep Hole
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful home with everything needed for comfort and a great time! Great location for getting to the beach, shopping and dining out. Communication with host was very informative and helpful. Thank you Chip!"
United States
Gil R.
The price is CA $121
CA $327 total
includes taxes & fees
Feb 10 - Feb 11
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
North Ocean City
10.0 out of 10, Exceptional, (1 review)
"We greatly enjoyed our stay at the Ocean City condo. The view from the porch was stunning. The condo was clean, spacious and well decorated. We hope to visit again next summer!"
United States
Jenna A.
The price is CA $135
CA $374 total
includes taxes & fees
Feb 11 - Feb 12
Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

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, (42 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $144
CA $547 total
includes taxes & fees
Feb 9 - Feb 10
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
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.