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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, (668 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $169
CA $190 total
includes taxes & fees
Nov 30 - Dec 1
Key West Cottages

2. 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 $237
CA $509 total
includes taxes & fees
Nov 2 - Nov 3
Pet-friendly creekside cottage w/ backyard

3. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (72 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is CA $133
CA $632 total
includes taxes & fees
Nov 18 - Nov 19
Bayfront Modern Retreat • Dock, Kayaks, Views

4. 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 $166
CA $550 total
includes taxes & fees
Nov 2 - Nov 3
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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 $145
CA $270 total
includes taxes & fees
Nov 2 - Nov 3
Assateageue Inn 104 by Seaside Vacations & Sales

6. Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (401 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 8 - Nov 9
Shore Point Cottages

7. 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)
"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 $283 total
includes taxes & fees
Nov 1 - Nov 2
Assateague Inn 111 by Seaside Vacations & Sales

8. 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 $225
CA $638 total
includes taxes & fees
Nov 3 - Nov 4
The purple door at the bay.

9. 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, (1,331 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 $140
CA $156 total
includes taxes & fees
Nov 28 - Nov 29
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

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, (85 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $147
CA $386 total
includes taxes & fees
Nov 30 - Dec 1
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

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, (10 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is CA $117
CA $376 total
includes taxes & fees
Nov 1 - Nov 2
Central Location~Walk 2 Dining! Beach Pass & Gear!

12. 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 $182
CA $459 total
includes taxes & fees
Oct 31 - Nov 1
Misty Mare Townhouse - Gorgeous home on Chincoteague Island

13. Luxury Home, 1.5mi to Assateague Island and Top Golf Courses! Sleeps 12!

Luxury Home, 1.5mi to Assateague Island and Top Golf Courses! Sleeps 12!
Berlin
10.0 out of 10, Exceptional, (105 reviews)
"Everything was great"
United States
Mike D.
The price is CA $560
CA $1,625 total
includes taxes & fees
Nov 23 - Nov 24
Luxury Home, 1.5mi to Assateague Island and Top Golf Courses! Sleeps 12!

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 $145
CA $270 total
includes taxes & fees
Nov 5 - Nov 6
Assateague Inn 213 by Seaside Vacations & Sales

15. Assateague Inn 100 by Seaside Vacations & Sales

Assateague Inn 100 by Seaside Vacations & Sales
Chincoteague
8.6 out of 10, Excellent, (13 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 $145
CA $270 total
includes taxes & fees
Nov 2 - Nov 3
Assateague Inn 100 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, (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 $189
CA $506 total
includes taxes & fees
Nov 1 - Nov 2
Comfortable cottage in gated community, 5 mins to OC and Assateague

17. Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (10 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
The price is CA $145
CA $283 total
includes taxes & fees
Nov 1 - Nov 2
Assateague Inn 106 by Seaside Vacations & Sales

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"Had great mini vac . The vrbo was right down town lots great shops and good choices for meals. All ready thinking about going back"
United States
Jeffry C.
The price is CA $106
CA $325 total
includes taxes & fees
Nov 5 - Nov 6
On Main Street - Apartment C - Berlin, MD

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 $173
CA $318 total
includes taxes & fees
Nov 1 - Nov 2
Assateague Inn 110 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.