A beach with gentle waves and a clear sky.

Assateague Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Assateague Island vacation rentals

A waterfront house with a balcony, dock, and a view of the water.

1. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (662 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $271
CA $304 total
includes taxes & fees
Nov 19 - Nov 20
Key West Cottages
A covered porch with wicker chairs and a view of the outdoors.

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 $232
CA $480 total
includes taxes & fees
Oct 27 - Oct 28
Pet-friendly creekside cottage w/ backyard
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

3. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (71 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is CA $126
CA $631 total
includes taxes & fees
Oct 21 - Oct 22
Bayfront Modern Retreat • Dock, Kayaks, Views
A two-story building with a central entrance and a wooden walkway leading to it.

4. 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 $146
CA $289 total
includes taxes & fees
Oct 28 - Oct 29
Assateague Inn 213 by Seaside Vacations & Sales
A sunroom with wicker furniture, large windows, and a view of the water.

5. 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 $237
CA $656 total
includes taxes & fees
Oct 21 - Oct 22
The purple door at the bay.
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.

6. 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 $146
CA $285 total
includes taxes & fees
Oct 26 - Oct 27
Assateageue Inn 104 by Seaside Vacations & Sales
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, (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 $168
CA $583 total
includes taxes & fees
Oct 21 - Oct 22
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

8. 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 $138
CA $409 total
includes taxes & fees
Nov 3 - Nov 4
Central Location~Walk 2 Dining! Beach Pass & Gear!
A beach with waves and a sunset.

9. 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, (83 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is CA $162
CA $404 total
includes taxes & fees
Nov 19 - Nov 20
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

10. 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, (1,330 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 $147
CA $164 total
includes taxes & fees
Oct 30 - Oct 31
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

11. 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 $463 total
includes taxes & fees
Oct 23 - Oct 24
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A covered patio with a table and chairs, overlooking a beach.

12. Majestic Hotel & Apartments

Majestic Hotel & Apartments
2.0 star property
Downtown Ocean City
5.8 out of 10, (531 reviews)
"Right in front of the board walk and almost center to everything"
United States
Wilber
The price is CA $90
CA $108 total
includes taxes & fees
Oct 21 - Oct 22
Majestic Hotel & Apartments
A house surrounded by dense trees and a wooden dock extending into a body of water.

13. 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 $168
CA $583 total
includes taxes & fees
Nov 1 - Nov 2
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.

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 $146
CA $284 total
includes taxes & fees
Oct 21 - Oct 22
Assateague Inn 111 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

15. 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 $161
CA $307 total
includes taxes & fees
Oct 28 - Oct 29
Assateague Inn 203 by Seaside Vacations & Sales
A beachside boardwalk with shops, a Ferris wheel, and a tram.

16. 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 $109
CA $334 total
includes taxes & fees
Oct 21 - Oct 22
On Main Street - Apartment C - Berlin, MD
A large outdoor swimming pool with people swimming and lounging, surrounded by a fence and shaded areas.

17. 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 $190
CA $509 total
includes taxes & fees
Oct 22 - Oct 23
Comfortable cottage in gated community, 5 mins to OC and Assateague
A living room with a sofa, ottoman, and dining table with chairs. There is a television on the wall and a window with a view of the outside.

18. 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 $175
CA $319 total
includes taxes & fees
Oct 22 - Oct 23
Assateague Inn 110 by Seaside Vacations & Sales
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
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 $146
CA $289 total
includes taxes & fees
Nov 3 - Nov 4
Assateague Inn 100 by Seaside Vacations & Sales
A living room with a blue sofa, a wooden dining table with chairs, a TV, and a balcony with blue curtains.

20. 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 $146
CA $289 total
includes taxes & fees
Nov 3 - Nov 4
Assateague Inn 106 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

Fenwick Inn

Fenwick Inn

10/10 Excellent
"It was great! Clean room. Staff was great!"
Jeanne 2-night trip
Posted 9 hours ago
Fenwick Inn

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 $90 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.