A beach with gentle waves and a clear sky.

Assateague Island Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Assateague Island vacation rentals

Palm Cottage | 1 bedroom, premium bedding, laptop workspace, soundproofing

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (615 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
$242 nightly
The price is $272
Sep 8 - Sep 9
Total with taxes and fees
Key West Cottages
Exterior

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (309 reviews)
"Experience was amazing! Amenities great! Clean resort, quiet, relaxing…all we hoped for! Will be back!!!!"
United States
Christine
$285 nightly
The price is $320
Aug 20 - Aug 21
Total with taxes and fees
Blufin Bungalows & Marina
Interior

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.
$420 nightly
The price is $460
Aug 25 - Aug 26
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
Outdoor dining

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.
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
House (3 Bedrooms) | Interior

5. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
$315 nightly
The price is $354
Aug 20 - Aug 21
Total with taxes and fees
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Smart TV, offices

6. 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.
$490 nightly
The price is $540
Sep 1 - Sep 2
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
TV, DVD player

7. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (30 reviews)
"Had a great stay! Place was very clean and host was great a communication."
United States
Jen G.
$202 nightly
The price is $212
Sep 14 - Sep 15
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
Beach nearby, sun loungers

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.
$406 nightly
The price is $456
Sep 7 - Sep 8
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
TV, DVD player

9. 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
$409 nightly
The price is $451
Aug 23 - Aug 24
Total with taxes and fees
The purple door at the bay.
Beach nearby

10. 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.
$489 nightly
The price is $549
Sep 8 - Sep 9
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Deluxe Cottage | View from room

11. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.2 out of 10, Wonderful, (357 reviews)
"Perfect space!"
United States
Brandi
$87 nightly
The price is $98
Sep 13 - Sep 14
Total with taxes and fees
Shore Point Cottages
Exterior

12. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very Good, (35 reviews)
"The location was central with a deck out on the marsh, which was lovely. The pool seemed well kept and was nice. It was clean and the communication with the hosts was quite good. The smart TVs didn’t really work and could only work with live tv. No apps worked. Overall, though, would stay again."
United States
Erin
$199 nightly
The price is $209
Sep 1 - Sep 2
Total with taxes and fees
Assateague Inn 111 by Seaside Vacations & Sales
Coffee/tea maker, fridge, microwave, oven

13. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (22 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.
$229 nightly
The price is $257
Aug 19 - Aug 20
Total with taxes and fees
Cozy Barn Loft: Country Views & Central to Beaches
Deluxe Apartment, 4 Bedrooms, Non Smoking, Ocean View | Terrace/patio

14. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (475 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
$93 nightly
The price is $105
Sep 1 - Sep 2
Total with taxes and fees
Majestic Hotel & Apartments
Smart TV, books

15. 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.
$303 nightly
The price is $340
Sep 8 - Sep 9
Total with taxes and fees
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Outdoor dining

16. 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.
$343 nightly
The price is $384
Sep 13 - Sep 14
Total with taxes and fees
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Outdoor pool

17. 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, (52 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
$400 nightly
The price is $448
Sep 1 - Sep 2
Total with taxes and fees
Comfortable cottage in gated community, 5 mins to OC and Assateague
Beach nearby

18. 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.
$266 nightly
The price is $298
Aug 24 - Aug 25
Total with taxes and fees
On Main Street - Apartment C - Berlin, MD
Property grounds

19. 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.
$1,026 nightly
The price is $1,090
Aug 18 - Aug 19
Total with taxes and fees
5 Bed/3.5 Bath in Bayside near West Ocean City
Apartment (2 Bedrooms) | Front of property

20. 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
Balcony w/ Inlet View: Dtwn Ocean City Condo
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

Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"The room was awesome, the hotel itself was beautiful, the only issue we had and most others as well, were the halls were too hot, felt like a sauna. The rooms were nice and cool though. I loved that they had a pool and arcade for the kids, a laundry room, vending machines, etc. Hotel was very close to the beach and restaurants which was nice, easily accessible walking distance. The balcony view was nice, loved the red chairs to sit out there at night. It was definitely a nice experience with my family."
Jose 1-night trip
Posted 1 hour ago
Bonita Beach Hotel

Find out more about Assateague Island

Everything you need to know about Assateague Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Assateague Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Assateague Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Assateague Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Assateague Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Assateague Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $76 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Assateague Island rentals

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