Holiday Homes in Assateague Island

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Holiday Homes in Assateague Island

Our top choices for Assateague Island holiday homes

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (178)
"Super cute cottages for a weekend getaway! Right on the water too."
Blufin Bungalows & Marina

The purple door at the bay.

9.2 out of 10, Wonderful, (52)
"We loved the view and can not wait to go back!"
The price is AU$691
includes taxes & fees
18 Sept - 19 Sept
The purple door at the bay.

Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

9.8 out of 10, Exceptional, (17)
"Would stay again "
The price is AU$724
includes taxes & fees
24 Sept - 25 Sept
Beach Paradise IX - Luxury 4-Bedrooms BOARDWALK Townhouse with Garage!

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

10.0 out of 10, Exceptional, (91)
"The property was great. Large kitchen, comfortable beds, and an amazing outdoor area. Laurie was friendly, responsive, and very accommodating. "
The price is AU$490
includes taxes & fees
10 Sept - 11 Sept
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BUILT in 2024-Canal Front, Pool, Swim Up & Covered Bar

10.0 out of 10, Exceptional, (10)
"Lovely location, great accommodations, speedy responses."
BUILT in 2024-Canal Front, Pool, Swim Up & Covered Bar

Wave Watcher's Condo - Steps to the beach!

9.8 out of 10, Exceptional, (9)
"My family and I enjoyed our stay at Wave Watchers! There were 9 of us and we had a comfortable stay! We would absolutely stay again because of the perfect location, cleanliness of the condo and communication to management for all of our needs. Highly recommended! "
Wave Watcher's Condo - Steps to the beach!

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

9.8 out of 10, Exceptional, (135)
"The accommodation were perfect and right down the street from the event we were attending. "
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Outstanding large Beach House on the Ocean Side with a private heated Pool!

9.2 out of 10, Wonderful, (52)
"We had a wonderful stay! The house was clean, modern, spacious, in a perfect location 2 minute walk to the beach, next to Royal Farms and across from Matt’s Fish Camp! Frank was very responsive, kind, and he truly cared for us to have the best stay at his vacation home. The heated pool especially so early in the season was the cherry on top! Thank you and we look forward to returning next year!"
Outstanding large Beach House on the Ocean Side with a private heated Pool!

Family Friendly Townhome in desired Stewards Watch Community- 5mins to the beach

9.4 out of 10, Exceptional, (55)
"We had a great time all thanks to the owner for housing us for our senior beach week"
Family Friendly Townhome in desired Stewards Watch Community- 5mins to the beach

Stunning New Beach House in Bayside, 2 Master Suites, Fast WiFi, Turn Key!

10.0 out of 10, Exceptional, (11)
Stunning New Beach House in Bayside, 2 Master Suites, Fast WiFi, Turn Key!

Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

9.6 out of 10, Exceptional, (64)
"Our stay was very nice "
Enjoy Beautiful Views From This 3 BR 2 BA Home on Quiet Canal in Ocean Pines.

Charming Canal Water View Townhome with Outdoor Pool, WiFi & AC in Ocean City

10.0 out of 10, Exceptional, (8)
Charming Canal Water View Townhome with Outdoor Pool, WiFi & AC in Ocean City

Waterfront Getaway-walk to beach and local favorites!

10.0 out of 10, Exceptional, (36)
"Our 1st time in Maryland and it was wonderful!!"
Waterfront Getaway-walk to beach and local favorites!

Island Retreat - Lovely Marsh Views and Pet Friendly!

9.0 out of 10, Wonderful, (12)
"Quiet place with everything we needed to be comfortable for our 10th anniversary. We loved it & are looking forward to a return trip."
Island Retreat - Lovely Marsh Views and Pet Friendly!

Private 3-bedroom ranch, 7.5 miles from Bethany Beach, on a dead-end street.

9.4 out of 10, Exceptional, (18)
"Thank you John for the lovely stay! Our family enjoyed our stay and made so many memories. "
Private 3-bedroom ranch, 7.5 miles from Bethany Beach, on a dead-end street.

Quiet Beachfront Retreat with Private Balcony

8.4 out of 10, Very good, (28)
"This cute little space was perfect for what we were looking for. It’s close to the beach and within walking distance to lots of restaurants and activities. "
Quiet Beachfront Retreat with Private Balcony

Ocean Front 4 bedroom 3 bath

9.0 out of 10, Wonderful, (7)
"Recommendations for owner: providing some hand soaps for the bathrooms/kitchen, remove broken furniture, fix holes/leaks in ceilings, provide working vacuum to help with sand throughout the week (didn’t work), quick response on missing pillow cases but no response from owner about state of unit. Pictures are deceiving regarding quality. Drawers falling out of cabinets. Threatening message from owner on fridge which wasn’t a nice touch. Overall- the location was fantastic but the unit and the...
Ocean Front 4 bedroom 3 bath

Charming house & casita near the ocean with private pool, W/D & central AC

8.0 out of 10, Very good, (38)
"We are OC locals and did a staycation for my husband’s 52nd birthday. The property was spacious. The two houses in one location was great foe privacy."
Charming house & casita near the ocean with private pool, W/D & central AC

Congratulations! You have found one of the Best Vacation Homes in Fenwick

9.8 out of 10, Exceptional, (98)
"We stayed for a long weekend to celebrate a 70th birthday for mom. We had a total of 12 people in the house and it was spacious and clean. The 5 Master Bedrooms is great and the kids loved the pool. It’s sobclose to the beach and shops & restaurants. This was our first trip to Fenwick Island (we go to the Outer Banks every year as a family) and this may be a new spot for us. Highly recommend Storm Bait."
Congratulations! You have found one of the Best Vacation Homes in Fenwick

5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+

The price is AU$3,713
includes taxes & fees
28 Sept - 29 Sept
5BR/4BA-Oceanview-Pool-Sundeck-Bike-Theater-Game Room-Sleep 16+
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Assateague Island Hotel Reviews

Find out more about Assateague Island

Find out more about Assateague Island

Assateague Island Holiday Homes information

Number of reviews
Accommodation
606 Holiday Homes
Lowest Price
AU$490
Highest Price
AU$3,713

Explore a world of travel with Expedia

Explore a world of travel with Expedia