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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, (624 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is CA $301
CA $337 total
includes taxes & fees
Sep 23 - Sep 24
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (316 reviews)
"Loved sitting on the porch and just seeing water, water everywhere!!"
United States
David
The price is CA $184
CA $284 total
includes taxes & fees
Sep 16 - Sep 17
Blufin Bungalows & Marina

3. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (369 reviews)
"Good and cute environment"
United States
junghyun
The price is CA $94
CA $129 total
includes taxes & fees
Sep 13 - Sep 14
Shore Point Cottages

4. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (140 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
The price is CA $226
CA $468 total
includes taxes & fees
Oct 1 - Oct 2
Pet-friendly creekside cottage w/ backyard

5. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 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
The price is CA $217
CA $621 total
includes taxes & fees
Sep 13 - Sep 14
The purple door at the bay.

6. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (496 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is CA $98
CA $117 total
includes taxes & fees
Oct 5 - Oct 6
Majestic Hotel & Apartments

7. Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (18 reviews)
"This place was perfect. Beds were comfy, it had everything i needed in the kitchen, secluded enough to feel like you were alone with nature but close enough to drive to tourist attractions. Literally everything we we looking for. Added bonus was napping in the screened in porch."
United States
Jackie P.
The price is CA $212
CA $617 total
includes taxes & fees
Oct 5 - Oct 6
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

8. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (36 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
The price is CA $145
CA $270 total
includes taxes & fees
Sep 21 - Sep 22
Assateague Inn 111 by Seaside Vacations & Sales

9. 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 $160
CA $492 total
includes taxes & fees
Sep 16 - Sep 17
2 Mi to Downtown: Tranquil Abode in Chincoteague!

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, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $191
CA $605 total
includes taxes & fees
Sep 16 - Sep 17
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

11. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"Overall nice stay!"
United States
Becky S.
The price is CA $176
CA $681 total
includes taxes & fees
Sep 8 - Sep 9
Bayfront Modern Retreat • Dock, Kayaks, Views

12. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (33 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is CA $146
CA $273 total
includes taxes & fees
Sep 15 - Sep 16
Assateageue Inn 104 by Seaside Vacations & Sales

13. 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, (53 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
The price is CA $207
CA $521 total
includes taxes & fees
Sep 23 - Sep 24
Comfortable cottage in gated community, 5 mins to OC and Assateague

14. 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, (79 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $201
CA $454 total
includes taxes & fees
Sep 30 - Oct 1
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

15. 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, (111 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is CA $276
CA $524 total
includes taxes & fees
Sep 13 - Sep 14
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

16. 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, (131 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

17. 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 $179
CA $452 total
includes taxes & fees
Oct 1 - Oct 2
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (40 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 $119
CA $335 total
includes taxes & fees
Oct 5 - Oct 6
On Main Street - Apartment C - Berlin, MD

19. 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, (1,318 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 $152
CA $170 total
includes taxes & fees
Sep 7 - Sep 8
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

20. The Mallard Apartments

The Mallard Apartments
2.5 star property
Downtown Ocean City
5.8 out of 10, (57 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 $137
CA $174 total
includes taxes & fees
Sep 7 - Sep 8
The Mallard Apartments
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Assateague Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Assateague Island vacation rentals we have selected for you start as low as CA $112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Assateague Island rentals

At Expedia, we put the best Assateague Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Assateague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Assateague Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Assateague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.