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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, (675 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $164
CA $184 total
includes taxes & fees
Dec 15 - Dec 16
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (344 reviews)
"We had a wonderful stay! The bungalow was nice, clean, and peaceful. It was the perfect place to relax and unwind. Would definitely stay again!"
United States
Rebecca
The price is CA $123
CA $219 total
includes taxes & fees
Dec 15 - Dec 16
Blufin Bungalows & Marina

3. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (141 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 $242
CA $492 total
includes taxes & fees
Nov 15 - Nov 16
Pet-friendly creekside cottage w/ backyard

4. 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, (87 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $150
CA $400 total
includes taxes & fees
Dec 3 - Dec 4
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

5. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 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 $148
CA $263 total
includes taxes & fees
Nov 16 - Nov 17
Assateageue Inn 104 by Seaside Vacations & Sales

6. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (39 reviews)
"Great for a quick weekend trip! Everything in listing was as described"
United States
mckenzie S.
The price is CA $148
CA $274 total
includes taxes & fees
Nov 15 - Nov 16
Assateague Inn 111 by Seaside Vacations & Sales

7. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (405 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
The price is CA $114
CA $128 total
includes taxes & fees
Nov 16 - Nov 17
Shore Point Cottages

8. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (7 reviews)
"Ramsey is a great host and provided everything we needed!"
United States
Kendall M.
The price is CA $231
CA $413 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 2-bedroom house in Chincoteague

9. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (69 reviews)
"Great location"
United States
Rick K.
The price is CA $243
CA $603 total
includes taxes & fees
Nov 16 - Nov 17
The purple door at the bay.

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, (49 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $170
CA $561 total
includes taxes & fees
Nov 23 - Nov 24
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

11. Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (11 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is CA $116
CA $345 total
includes taxes & fees
Nov 16 - Nov 17
Central Location~Walk 2 Dining! Beach Pass & Gear!

12. 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, (1,332 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 $151 total
includes taxes & fees
Dec 4 - Dec 5
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

13. Coastal Retreat - EV Charger - Near Marina & Beaches

Coastal Retreat - EV Charger - Near Marina & Beaches
Captain's Cove
The price is CA $457
CA $548 total
includes taxes & fees
Nov 28 - Nov 29
Coastal Retreat - EV Charger - Near Marina & Beaches

14. 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, (21 reviews)
"This was an amazing property and a wonderful experience from start to finish."
United States
Benjamin G.
The price is CA $169
CA $557 total
includes taxes & fees
Nov 15 - Nov 16
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

15. Assateague Inn 105 by Seaside Vacations & Sales

Assateague Inn 105 by Seaside Vacations & Sales
Chincoteague Island
8.6 out of 10, Excellent, (19 reviews)
"As usual we had a wonderful stay at the Assateague Inn and cannot wait for our next visit. "
United States
Sarah M.
The price is CA $148
CA $276 total
includes taxes & fees
Dec 3 - Dec 4
Assateague Inn 105 by Seaside Vacations & Sales

16. Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Great stay!"
United States
Lauren P.
The price is CA $148
CA $276 total
includes taxes & fees
Nov 29 - Nov 30
Assateague Inn 213 by Seaside Vacations & Sales

17. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (12 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
The price is CA $148
CA $276 total
includes taxes & fees
Dec 9 - Dec 10
Assateague Inn 106 by Seaside Vacations & Sales

18. 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, (58 reviews)
"The cottage location is great for golf, less than 20 minutes ride to most courses. Also dining in Berlin is better than traffic to Oean City."
United States
Joe
The price is CA $193
CA $494 total
includes taxes & fees
Nov 16 - Nov 17
Comfortable cottage in gated community, 5 mins to OC and Assateague

19. Assateague Inn 110 by Seaside Vacations & Sales

Assateague Inn 110 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (12 reviews)
"The whole stay was excellent and the property was in an excellent location. Surprisingly quiet considering the proximity to restaurants and activities."
United States
Anonymous traveller
The price is CA $177
CA $308 total
includes taxes & fees
Nov 15 - Nov 16
Assateague Inn 110 by Seaside Vacations & Sales

20. Assateague Inn 100 by Seaside Vacations & Sales

Assateague Inn 100 by Seaside Vacations & Sales
Chincoteague
8.6 out of 10, Excellent, (14 reviews)
"Quiet area and close to all attractions. Very fast response with any questions before and during stay. Would recommend!"
United States
Sue S.
The price is CA $148
CA $274 total
includes taxes & fees
Nov 15 - Nov 16
Assateague Inn 100 by Seaside Vacations & Sales
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 $128 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.