Photo by Nancy Stauffer

Assateague Island holiday homes

We found 6,550 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Assateague Island

Showing deals for:1 Jan - 8 Jan

Pool
Marina
Interior
Room
Exceptional
(58 reviews)

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Chincoteague

8% off
NZ$4,070
for 7 nights, 1 cottage
NZ$581 per night
includes taxes & fees
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Living area
Pool
Private kitchen
Room
Exceptional
(23 reviews)

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Chincoteague

8% off
NZ$5,955
for 7 nights, 1 cottage
NZ$851 per night
includes taxes & fees
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Upstairs sunroom
Terrace/patio
Upstairs sunroom
Upstairs living room
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
NZ$2,769
for 7 nights, 1 apartment
NZ$396 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Property grounds
Exterior
Living area
Dining
Exceptional
(9 reviews)

Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague

Chincoteague

8% off
NZ$4,518
for 7 nights, 1 home
NZ$645 per night
includes taxes & fees
Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague
Room
Living area
Exterior
Private kitchen
Exceptional
(9 reviews)

Makai Sunset Cove all-season indoor pool

Ocean City

5% off
NZ$2,446
for 7 nights, 1 apartment
NZ$349 per night
includes taxes & fees
Makai Sunset Cove all-season indoor pool
Room
Property grounds
Living area
Exterior
Exceptional
(108 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
NZ$4,148
for 7 nights, 1 home
NZ$593 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Kitchen
Sunroom
Sunroom
Front Porch
Exceptional
(127 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
NZ$1,986
for 7 nights, 1 home
NZ$284 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Beach
Living area
Private kitchen
Pool
Exceptional
(58 reviews)

Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!

Ocean City

7% off
NZ$9,749
for 7 nights, 1 apartment
NZ$1,393 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Indoor Pool and hot tub
Living area
Living area
Atrium
Exceptional
(106 reviews)

Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay

Ocean City

8% off
NZ$7,124
for 7 nights, 1 apartment
NZ$1,018 per night
includes taxes & fees
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
Livingroom - view 2
Master bedroom balcony - Ocean front
View of main level - mid point
View of building
Exceptional
(20 reviews)

Unique Direct Oceanfront w/a Private Beach

Ocean City

8% off
NZ$14,988
for 7 nights, 1 home
NZ$2,141 per night
includes taxes & fees
Unique Direct Oceanfront w/a Private Beach
Fire pit patio. You will need to bring your own wood.
Living room from kitchen
Queen room 1 with en-suite bathroom
Living room and dining room
Exceptional
(161 reviews)

The Brass Crab - Check in/out any day!

Chincoteague

7% off
NZ$2,638
for 7 nights, 1 home
NZ$377 per night
includes taxes & fees
The Brass Crab - Check in/out any day!
Room
Interior
Living area
Living area
Exceptional
(55 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
NZ$2,605
for 7 nights, 1 apartment
NZ$372 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Property grounds
Great sunset views of the bay!
Exterior
Nice fireplace with 50” flatscreen tv above
Exceptional
(150 reviews)

BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!

Ocean City

8% off
NZ$2,493
for 7 nights, 1 apartment
NZ$356 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Dining
Dining
Living area
Exterior
Exceptional
(16 reviews)

LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens

Ocean City

8% off
NZ$6,294
for 7 nights, 1 apartment
NZ$899 per night
includes taxes & fees
LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens
Private kitchen
Exterior
Outdoor dining
Property grounds
Exceptional
(13 reviews)

Lorelei Condo - Watch Fireworks From Balcony!

Ocean City

5% off
NZ$2,672
for 7 nights, 1 apartment
NZ$382 per night
includes taxes & fees
Lorelei Condo - Watch Fireworks From Balcony!
02-1Q7A9645
25-1Q7A9621
26-1Q7A9624
29-01-DJI_0993
Wonderful
(5 reviews)

Blush & Blue at the Irene – Beachfront Balcony + Heated Pool (Open Until October 26th 2026)

Ocean City

5% off
NZ$2,259
for 7 nights, 1 home
NZ$323 per night
includes taxes & fees
Blush & Blue at the Irene – Beachfront Balcony + Heated Pool (Open Until October 26th 2026)
Private kitchen
View from the Kitchen and living room. Back Deck
Room
Living area
Exceptional
(31 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
NZ$6,493
for 7 nights, 1 home
NZ$928 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
KT+vfw
Living area
06-1Q7A4263
ext+deck+vfne
Exceptional
(8 reviews)

Biscayne Bungalow– Coastal Charm Near the Beach

Ocean City

5% off
NZ$3,854
for 7 nights, 1 home
NZ$551 per night
includes taxes & fees
Biscayne Bungalow– Coastal Charm Near the Beach
Breathtaking nighttime view from the condo
view from balcony to living area
Relax, Have dinner, Play games, see the ocean!
Ocean Front view of the Pyramid the most unique building on the beach
Exceptional
(102 reviews)

Escape to The Ocean! , Ocean Front, Beautiful View, Pool!

Ocean City

7% off
NZ$2,344
for 7 nights, 1 apartment
NZ$335 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Private kitchen
Pool
Room
Interior
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

8% off
NZ$3,776
for 7 nights, 1 apartment
NZ$539 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
Private kitchen
Exterior
Interior
Living area
Exceptional
(92 reviews)

Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.

Ocean City

8% off
NZ$4,257
for 7 nights, 1 apartment
NZ$608 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Bedroom with Two Full-Size Beds & Flat-Screen HDTV
Winter is a Great Time to Enjoy the Beach!
Lit Entry Hall to Condo - Front Door on Right.
Indoor Pool (Open Summer months Only)
Exceptional
(31 reviews)

Direct Ocean Front...In The Middle of it All!!!

Ocean City

6% off
NZ$7,280
for 7 nights, 1 apartment
NZ$1,040 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Living area
04-Unit A-04
31-Unit B-05
36-Unit B-10
Exceptional
(5 reviews)

Dorchester Drift B: Shore Nest

Ocean City

5% off
NZ$3,107
for 7 nights, 1 home
NZ$444 per night
includes taxes & fees
Dorchester Drift B: Shore Nest
Dining
Living area
Room
Private kitchen
Exceptional
(102 reviews)

3BR Newly Renovated Oceanfront Condo BOARDWALK 24' long Balcony Regency10atOCMD

Ocean City

8% off
NZ$4,401
for 7 nights, 1 apartment
NZ$629 per night
includes taxes & fees
3BR Newly Renovated Oceanfront Condo BOARDWALK 24' long Balcony Regency10atOCMD
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Assateague Island getaway

Learn about the unique charm of Assateague Island with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Assateague Island

Are you searching for attractions to see during your stay? Venture out of your holiday home and experience everything that Assateague Island has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Maui Jack's Waterpark (10.7 mi / 17.3 km)
  • Frontier Town Water Park and Golf (17.2 mi / 27.6 km)
  • Trimper's Rides (20.6 mi / 33.1 km)
  • Jolly Roger at the Pier (20.7 mi / 33.3 km)
  • Jolly Roger Amusement Park (22.9 mi / 36.9 km)
  • Carousel Ice Skating Rink (27.4 mi / 44 km)

Exploring the natural features in Assateague Island

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Assateague Island is a great place to spend some time outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Ocean City Beach (20.6 mi / 33.2 km)
  • Chincoteague National Wildlife Refuge (8 mi / 12.9 km)
  • Assateague Point (13.4 mi / 21.5 km)
  • Ocean City Inlet (20.4 mi / 32.8 km)
  • Inlet Park (20.5 mi / 33 km)
  • Assawoman Bay (26.9 mi / 43.4 km)

Frequently asked questions

How much does it cost to rent a holiday home in Assateague Island?
Length of stay, property type and season are some factors that can affect the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy cabins to expansive villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Assateague Island?
The average price for a holiday home near the beach in Assateague Island depends on when you're travelling and the style and size of property you're looking for. You can easily and quickly find prices on Bookabach by entering your travel dates and destination. Then use our filters to choose the number of bedrooms and amenities that you prefer, such as a pool, WiFi and air conditioning.
How old do you have to be to rent a holiday home in Assateague Island?
The minimum age requirements can differ across properties on Bookabach, so double-check the rules of the holiday home in Assateague Island you want. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Assateague Island for?
It's up to the Assateague Island property. To see all available options offering extended stays, simply enter your travel dates and number of people into Bookabach's search page. Enjoy having the place to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces where the kids can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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