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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, (677 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $162
CA $182 total
includes taxes & fees
Dec 16 - Dec 17
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 16 - Dec 17
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 $470 total
includes taxes & fees
Nov 16 - Nov 17
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 $401 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 $276 total
includes taxes & fees
Nov 17 - Nov 18
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 $126
CA $165 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 $394 total
includes taxes & fees
Nov 16 - Nov 17
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 17 - Nov 18
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 $117
CA $347 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
Nov 28 - Nov 29
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 $537 total
includes taxes & fees
Nov 16 - Nov 17
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
Nov 30 - Dec 1
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 17 - Nov 18
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
Nov 17 - Nov 18
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 $297 total
includes taxes & fees
Nov 16 - Nov 17
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 $263 total
includes taxes & fees
Nov 16 - Nov 17
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

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.