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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 $302
CA $339 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 $195
CA $297 total
includes taxes & fees
Sep 7 - Sep 8
Blufin Bungalows & Marina

3. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (367 reviews)
"Good and cute environment"
United States
junghyun
The price is CA $112
CA $149 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 $343
CA $615 total
includes taxes & fees
Sep 28 - Sep 29
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 $218
CA $620 total
includes taxes & fees
Sep 15 - Sep 16
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, (495 reviews)
"Great location--Very close to the steps and boardwalk!"
United States
ALEXIS
The price is CA $111
CA $131 total
includes taxes & fees
Sep 8 - Sep 9
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 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 CA $222
CA $650 total
includes taxes & fees
Sep 2 - Sep 3
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 $269 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 $170
CA $506 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 $187
CA $599 total
includes taxes & fees
Sep 2 - Sep 3
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 $161
CA $663 total
includes taxes & fees
Sep 2 - Sep 3
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, (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 CA $146
CA $270 total
includes taxes & fees
Sep 14 - Sep 15
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 $208
CA $531 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 $194
CA $437 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 $277
CA $526 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.
The price is CA $478
CA $865 total
includes taxes & fees
Oct 1 - Oct 2
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 $180
CA $447 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 $156
CA $390 total
includes taxes & fees
Sep 13 - Sep 14
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 $111
CA $125 total
includes taxes & fees
Sep 17 - Sep 18
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, (56 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 $123
CA $159 total
includes taxes & fees
Sep 8 - Sep 9
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

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.