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Assateague Island Vacation Rentals

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Our top choices for Assateague Island vacation rentals

1. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (320 reviews)
"Loved sitting on the porch and just seeing water, water everywhere!!"
United States
David
The price is CA $193
CA $294 total
includes taxes & fees
Sep 13 - Sep 14
Blufin Bungalows & Marina

2. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (631 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 $338 total
includes taxes & fees
Sep 13 - Sep 14
Key West Cottages

3. 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 $464 total
includes taxes & fees
Oct 1 - Oct 2
Pet-friendly creekside cottage w/ backyard

4. 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 $153
CA $485 total
includes taxes & fees
Sep 16 - Sep 17
2 Mi to Downtown: Tranquil Abode in Chincoteague!

5. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (374 reviews)
"Good and cute environment"
United States
junghyun
The price is CA $123
CA $161 total
includes taxes & fees
Sep 13 - Sep 14
Shore Point Cottages

6. 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 $140
CA $264 total
includes taxes & fees
Sep 28 - Sep 29
Assateague Inn 213 by Seaside Vacations & Sales

7. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 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 $140
CA $264 total
includes taxes & fees
Sep 16 - Sep 17
Assateageue Inn 104 by Seaside Vacations & Sales

8. 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 CA $191
CA $378 total
includes taxes & fees
Sep 11 - Sep 12
Cozy Barn Loft: Country Views & Central to Beaches

9. 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 $201
CA $611 total
includes taxes & fees
Sep 14 - Sep 15
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

10. 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 $205
CA $453 total
includes taxes & fees
Sep 13 - Sep 14
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

11. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
10.0 out of 10, Exceptional, (18 reviews)
"Great location, easy check in, very clean, well decorated"
United States
sue g.
The price is CA $179
CA $448 total
includes taxes & fees
Oct 1 - Oct 2
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

12. 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 $251
CA $776 total
includes taxes & fees
Sep 27 - Sep 28
Bayfront Modern Retreat • Dock, Kayaks, Views

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (41 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 $341 total
includes taxes & fees
Oct 5 - Oct 6
On Main Street - Apartment C - Berlin, MD

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, (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 $216
CA $628 total
includes taxes & fees
Sep 21 - Sep 22
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

15. 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 CA $154
CA $282 total
includes taxes & fees
Sep 22 - Sep 23
Assateague Inn 203 by Seaside Vacations & Sales

16. 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, (54 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 $186
CA $492 total
includes taxes & fees
Sep 23 - Sep 24
Comfortable cottage in gated community, 5 mins to OC and Assateague

17. Assateague Inn 100 by Seaside Vacations & Sales

Assateague Inn 100 by Seaside Vacations & Sales
Chincoteague
9.0 out of 10, Wonderful, (11 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 $140
CA $263 total
includes taxes & fees
Sep 13 - Sep 14
Assateague Inn 100 by Seaside Vacations & Sales

18. 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 $140
CA $264 total
includes taxes & fees
Sep 21 - Sep 22
Assateague Inn 111 by Seaside Vacations & Sales

19. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (503 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
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.