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Assateague Island Holiday Rentals

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Our top choices for Assateague Island holiday rentals

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (623 reviews)
"Absolutely loved our stay. It was so quiet, peaceful and scenic. The pool was amazing"
United States
Lindsay
The price is NZ$414
includes taxes & fees
7 Sept - 8 Sept
Key West Cottages

2. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (364 reviews)
"Good and cute environment"
United States
junghyun
The price is NZ$184
includes taxes & fees
13 Sept - 14 Sept
Shore Point Cottages

3. 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 NZ$615
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Downtown: Tranquil Abode in Chincoteague!

4. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (32 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 NZ$333
includes taxes & fees
14 Sept - 15 Sept
Assateageue Inn 104 by Seaside Vacations & Sales

5. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place. I’ve stayed at Assateague Inn on several occasions over the years but this was my first time in 203 and by far the nicest one I’ve stayed in. Newly renovated and tastefully d"
United States
Annette H.
The price is NZ$342
includes taxes & fees
13 Sept - 14 Sept
Assateague Inn 203 by Seaside Vacations & Sales

6. 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 NZ$725
includes taxes & fees
30 Aug - 31 Aug
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

7. 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 NZ$804
includes taxes & fees
1 Sept - 2 Sept
Bayfront Modern Retreat • Dock, Kayaks, Views

8. 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 NZ$738
includes taxes & fees
28 Sept - 29 Sept
Pet-friendly creekside cottage w/ backyard

9. 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 NZ$754
includes taxes & fees
4 Sept - 5 Sept
The purple door at the bay.

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

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 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.
The price is NZ$449
includes taxes & fees
30 Aug - 31 Aug
Cozy Barn Loft: Country Views & Central to Beaches

11. 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 NZ$579
includes taxes & fees
27 Sept - 28 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

12. 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 NZ$558
includes taxes & fees
8 Sept - 9 Sept
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

13. 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 family friendly home was well appointed and offered the comforts of home. The host thought of everything you might need or want for your vacation. We hope to stay there again soon. The time that was put into getting this home ready for guests was very appreciated. Thank you David and Veronica"
United States
Jennifer
The price is NZ$789
includes taxes & fees
31 Aug - 1 Sept
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

14. 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 NZ$636
includes taxes & fees
21 Sept - 22 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague

15. 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 NZ$483
includes taxes & fees
2 Sept - 3 Sept
On Main Street - Apartment C - Berlin, MD

16. 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 NZ$331
includes taxes & fees
1 Sept - 2 Sept
Assateague Inn 111 by Seaside Vacations & Sales

17. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (490 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is NZ$160
includes taxes & fees
1 Sept - 2 Sept
Majestic Hotel & Apartments

18. 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 NZ$642
includes taxes & fees
13 Sept - 14 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

19. OCHG VIRGINIA LEE

OCHG VIRGINIA LEE
2.0 star property
Downtown Ocean City
7.8 out of 10, Good, (9 reviews)
"Love the quaintness of the property. Very clean. Needs updating however did have the old school beach vibe. Really enjoyed our stay. "
United States
Kimberly
The price is NZ$783
includes taxes & fees
7 Sept - 8 Sept
OCHG VIRGINIA LEE

20. 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, (1,317 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 NZ$151
includes taxes & fees
14 Sept - 15 Sept
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Assateague Island holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Assateague Island. 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 Assateague Island. 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 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 holiday 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 Assateague Island short-term rentals, that won’t be hard to do.