A beach with gentle waves and a clear sky.

Search Vacation Homes in Assateague Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 homes

1. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (328 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is ￥22,438
￥34,006 total
includes taxes & fees
Oct 13 - Oct 14
Blufin Bungalows & Marina
A sunroom with wicker furniture, large windows, and a view of the water.

2. 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 ￥24,776
￥70,880 total
includes taxes & fees
Sep 23 - Sep 24
The purple door at the bay.
A cozy living room with a sofa, a coffee table, and a TV mounted on the wall.

3. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (6 reviews)
"The host was very responsive and brought toys over for our children to help occupy them while we were there. The host is also connected to the Daisey's Island Cruises and gave us a discounted price to take in the cruise while we were on the island. That was very enjoyable and helped us learn more about the island and the annual pony round-up. It suited our family of 5 well."
United States
Cleason H.
The price is ￥25,556
￥47,552 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 2-bedroom house in Chincoteague
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

4. 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 ￥31,462
￥60,432 total
includes taxes & fees
Sep 23 - Sep 24
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
A sandy beach with footprints and a person walking.

5. 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 ￥18,669
￥62,015 total
includes taxes & fees
Oct 1 - Oct 2
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A covered porch with a red swing chair, white chairs, and a view of the street.

6. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay close to town. Charming screened porch, well appointed kitchen, plenty of space for us."
United States
Veronika B.
The price is ￥25,170
￥75,788 total
includes taxes & fees
Sep 23 - Sep 24
The Neigh-Neigh - Location! Location! Location!
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

7. 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 ￥20,592
￥78,411 total
includes taxes & fees
Sep 27 - Sep 28
Bayfront Modern Retreat • Dock, Kayaks, Views
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.

8. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
9.8 out of 10, Exceptional, (9 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A living room with a sofa, ottoman, and a lamp. There is a television mounted on the wall and a window with blinds.

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

Pool + Bay Access! Home 13 Mi to Ocean City Beach
Ocean Pines
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful weekend staying here. My kids loved riding their bikes around the community, to the Farmer's Market, and playground. The pool is super close and a great way to cool off after a day at the beach.The location is a short to drive to Ocean City to enjoy the beach and all their activities.The patio is very relaxing to enjoy eating crabs and dinners.The place is very clean, organized, and comfortable. It stayed nice and cool inside during the hot days and nights. The kitchen is well...
United States
Sandy
The price is ￥10,382
￥69,241 total
includes taxes & fees
Sep 23 - Sep 24
Pool + Bay Access! Home 13 Mi to Ocean City Beach
A beach with waves and a sunset.

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, (80 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is ￥19,113
￥46,373 total
includes taxes & fees
Sep 30 - Oct 1
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
A beachside view with a wooden deck, a chair, and a table.

11. 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, (16 reviews)
"Nice pet friendly accommodation. "
United States
Claudia w.
The price is ￥36,024
￥45,931 total
includes taxes & fees
Oct 2 - Oct 3
Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

12. 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 ￥18,169
￥47,770 total
includes taxes & fees
Sep 28 - Sep 29
Central Location~Walk 2 Dining! Beach Pass & Gear!
A kitchen with a farmhouse sign, a clock, and a refrigerator.

13. 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 ￥21,803
￥42,568 total
includes taxes & fees
Sep 23 - Sep 24
Cozy Barn Loft: Country Views & Central to Beaches
A modern living room with a sofa, coffee table, dining table, and chairs. There is a TV mounted on the wall and artwork above the table.

14. BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED

BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
Downtown Ocean City
10.0 out of 10, Exceptional, (4 reviews)
"The house was as listed, it was an enjoyable stay. Ann was easy to work with. Thanks VRBO."
United States
Anonymous traveler
The price is ￥14,944
￥57,437 total
includes taxes & fees
Sep 28 - Sep 29
BeachParadise107-OCEANVIEW Townhome-Steps to BEACH and BOARDWALK-LINENS INCLUDED
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

15. 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 ￥20,394
￥51,444 total
includes taxes & fees
Oct 5 - Oct 6
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A spacious kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

16. Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (34 reviews)
"Great vacation area and accommodation!"
United States
Letizia
The price is ￥14,944
￥56,556 total
includes taxes & fees
Oct 5 - Oct 6
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
A house surrounded by dense trees and a wooden dock extending into a body of water.

17. 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 ￥26,302
￥75,153 total
includes taxes & fees
Sep 23 - Sep 24
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
A marina with boats docked, wooden chairs on a deck, and houses in the background.

18. Charming 4-bedroom Beach House in Ocean Pines

Charming 4-bedroom Beach House in Ocean Pines
Ocean Pines
9.8 out of 10, Exceptional, (17 reviews)
"The house was so nice! Highly recommend this property"
United States
Anonymous traveler
The price is ￥58,047
￥110,469 total
includes taxes & fees
Sep 23 - Sep 24
Charming 4-bedroom Beach House in Ocean Pines
A dining area with a wooden table set for four, surrounded by wicker chairs.

19. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
North Ocean City
9.6 out of 10, Exceptional, (139 reviews)
"Great place to stay. There was plenty of room, easy access to close shopping."
United States
Rebecca D.
The price is ￥11,923
￥53,590 total
includes taxes & fees
Sep 28 - Sep 29
"BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE
A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

20. BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (159 reviews)
"Great house, location was excellent "
United States
Mike G.
The price is ￥11,798
￥52,151 total
includes taxes & fees
Oct 18 - Oct 19
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Assateague Island Hotel Reviews

Francis Scott Key Family Resort

Francis Scott Key Family Resort

8/10 Good
"I want to first highlight a gentleman by the name Donald; He was the nicest guy there., we arrived on Sunday. and the pools ware closed. now mind you it was after Labor Day weekend, but the main reason why I picked this place was because it showed on the website that the pool was still open outdoor and indoor. i went to the front desk the next day to ask why the pools weren't open the gentleman wasn't there. there were two ladies and the older one was extremely rude. I went back the next day to see if there was another person and I found Donald :) i mention to him the pool situation and he said I am so sorry about this yes, a lot of people that just got here have been having concerts about it. I will let the manager know. long story short he took care of it. we had a great time in the outdoor pool & indoor in the afternoon. it was a very nice place for my family, and I will definitely book my stay again next year. hoping that they will keep the pool open again. :)"
ALICIA 7-night trip
Posted 2 hours ago
Francis Scott Key Family Resort

Find out more about Assateague Island

Assateague Island Vacation Homes information

Number of reviews
730
Accommodation
652 Vacation Homes
Lowest Price
￥34,006
Highest Price
￥110,469