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Assateague Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (330 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is CA $201
CA $305 total
includes taxes & fees
Oct 13 - Oct 14
Blufin Bungalows & Marina
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

2. 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 $143
CA $480 total
includes taxes & fees
Sep 30 - Oct 1
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A waterfront house with a balcony, dock, and a view of the water.

3. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (645 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is CA $284
CA $319 total
includes taxes & fees
Oct 18 - Oct 19
Key West Cottages
A covered porch with wicker chairs and a view of the outdoors.

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 $230
CA $447 total
includes taxes & fees
Oct 1 - Oct 2
Pet-friendly creekside cottage w/ backyard
A two-story building with a central entrance and a wooden walkway leading to it.

5. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 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 $157
CA $287 total
includes taxes & fees
Sep 28 - Sep 29
Assateague Inn 203 by Seaside Vacations & Sales
A sunroom with wicker furniture, large windows, and a view of the water.

6. 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 $222
CA $595 total
includes taxes & fees
Oct 1 - Oct 2
The purple door at the bay.
A sandy beach with footprints and a person walking.

7. 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 $167
CA $581 total
includes taxes & fees
Sep 29 - Sep 30
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

8. 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 $181
CA $694 total
includes taxes & fees
Sep 27 - Sep 28
Bayfront Modern Retreat • Dock, Kayaks, Views
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

9. 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 $143
CA $270 total
includes taxes & fees
Oct 5 - Oct 6
Assateageue Inn 104 by Seaside Vacations & Sales
A kitchen with a farmhouse sign, a clock, and a refrigerator.

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)
The price is CA $195
CA $362 total
includes taxes & fees
Sep 26 - Sep 27
Cozy Barn Loft: Country Views & Central to Beaches
A beach with waves and a sunset.

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, (81 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $159
CA $403 total
includes taxes & fees
Sep 30 - Oct 1
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

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 $183
CA $432 total
includes taxes & fees
Oct 1 - Oct 2
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

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, (56 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 $190
CA $510 total
includes taxes & fees
Sep 27 - Sep 28
Comfortable cottage in gated community, 5 mins to OC and Assateague
A two-story building with a central entrance and a wooden walkway leading to it.

14. 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 $143
CA $270 total
includes taxes & fees
Sep 28 - Sep 29
Assateague Inn 111 by Seaside Vacations & Sales
A beachside boardwalk with shops, a Ferris wheel, and a tram.

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

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (42 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 $109
CA $335 total
includes taxes & fees
Oct 7 - Oct 8
On Main Street - Apartment C - Berlin, MD
A two-story building with a central entrance and a wooden walkway leading to it.

16. 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 $143
CA $270 total
includes taxes & fees
Oct 19 - Oct 20
Assateague Inn 213 by Seaside Vacations & Sales
A living room with a sofa, ottoman, and a lamp. There is a television mounted on the wall and a window with blinds.

17. Pool + Bay Access! Home 13 Mi to Ocean City Beach

Pool + Bay Access! Home 13 Mi to Ocean City Beach
3.0 star property
Ocean Pines
The price is CA $134
CA $603 total
includes taxes & fees
Sep 27 - Sep 28
Pool + Bay Access! Home 13 Mi to Ocean City Beach
A house surrounded by dense trees and a wooden dock extending into a body of water.

18. 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)
"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 $230
CA $661 total
includes taxes & fees
Oct 5 - Oct 6
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A two-story building with a central entrance and a wooden walkway leading to it.

19. 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 $143
CA $270 total
includes taxes & fees
Sep 28 - Sep 29
Assateague Inn 100 by Seaside Vacations & Sales
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

20. 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 $282
CA $542 total
includes taxes & fees
Sep 29 - Sep 30
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"Nice staff"
Mary Ellen 3-night trip
Posted less than an hour ago
Princess Royale Oceanfront Resort

Find out more about Assateague Island

Everything you need to know about Assateague Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Assateague Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Assateague Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Assateague Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Assateague Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Assateague Island vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Assateague Island vacation rentals we have selected for you start as low as CA $108 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Assateague Island rentals

At Expedia, we put the best Assateague Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Assateague Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Assateague Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Assateague Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.