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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, (653 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is CA $276
CA $310 total
includes taxes & fees
Oct 7 - Oct 8
Key West Cottages

2. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (334 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is CA $217
CA $324 total
includes taxes & fees
Oct 13 - Oct 14
Blufin Bungalows & Marina

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 CA $145
CA $486 total
includes taxes & fees
Oct 8 - Oct 9
2 Mi to Downtown: Tranquil Abode in Chincoteague!

4. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"We had a mommy-daughter mini-getaway to celebrate her 9th birthday! The area is very walkable, but also easy to drive and navigate the rest of the island. Our room was clean, as advertised, and the perfect place to relax, eat, and recharge. We loved the pool! The check-in/check-out process was very easy."
United States
Nora T.
The price is CA $163
CA $293 total
includes taxes & fees
Oct 7 - Oct 8
Assateague Inn 203 by Seaside Vacations & Sales

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 $275 total
includes taxes & fees
Oct 7 - Oct 8
Assateageue Inn 104 by Seaside Vacations & Sales

6. 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 $233
CA $482 total
includes taxes & fees
Oct 7 - Oct 8
Pet-friendly creekside cottage w/ backyard

7. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (69 reviews)
"Overall nice stay!"
United States
Becky S.
The price is CA $162
CA $679 total
includes taxes & fees
Oct 7 - Oct 8
Bayfront Modern Retreat • Dock, Kayaks, Views

8. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
9.8 out of 10, Exceptional, (19 reviews)
"Great location, easy check in, very clean, well decorated"
United States
sue g.
The price is CA $185
CA $463 total
includes taxes & fees
Oct 15 - Oct 16
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

9. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 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 $224
CA $642 total
includes taxes & fees
Oct 12 - Oct 13
The purple door at the bay.

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

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (10 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is CA $146
CA $412 total
includes taxes & fees
Oct 19 - Oct 20
Central Location~Walk 2 Dining! Beach Pass & Gear!

11. 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 $170
CA $589 total
includes taxes & fees
Oct 7 - Oct 8
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

12. 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, (20 reviews)
"Beautiful, clean, well appointed house in a peaceful setting. Easy & quick (20 minute) access to Assateague & Ocean City beaches without the chaos of staying in OC. Berlin and Snow Hill are fun historic eastern shore towns to explore. Take a day trip south to Pokomoke State Park for a calming non-beach nature experience. So nice we booked it again on our first day there."
United States
David M.
The price is CA $177
CA $584 total
includes taxes & fees
Nov 3 - Nov 4
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

13. 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, (82 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $164
CA $405 total
includes taxes & fees
Nov 3 - Nov 4
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

14. 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
Oct 20 - Oct 21
Assateague Inn 213 by Seaside Vacations & Sales

15. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (388 reviews)
"Everything was clean and comfortable. Would stay here again."
United States
Kelly
Shore Point Cottages

16. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (37 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 $148
CA $276 total
includes taxes & fees
Oct 13 - Oct 14
Assateague Inn 111 by Seaside Vacations & Sales

17. 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 $310 total
includes taxes & fees
Oct 7 - Oct 8
Assateague Inn 110 by Seaside Vacations & Sales

18. 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 $148
CA $275 total
includes taxes & fees
Oct 7 - Oct 8
Assateague Inn 100 by Seaside Vacations & Sales

19. Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (17 reviews)
"Nice pet friendly accommodation. "
United States
Claudia w.
Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 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 $110
CA $334 total
includes taxes & fees
Oct 7 - Oct 8
On Main Street - Apartment C - Berlin, MD
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.