Photo by Nancy Stauffer

Assateague Island holiday rentals

We found 6,532 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Assateague Island

Showing deals for:20 Nov - 27 Nov

Living area
Private kitchen
Exterior
Room
Exceptional
(29 reviews)

Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in

Berlin

8% off
AU$3,596
for 7 nights, 1 home
AU$514 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Exterior
Beautifully decorated, comfortable, clean home
Private kitchen
Dining
Exceptional
(161 reviews)

Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

Chincoteague

7% off
AU$2,107
for 7 nights, 1 home
AU$301 per night
includes taxes & fees
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
Dining
Exterior
Living area
Property grounds
Exceptional
(7 reviews)

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

Chincoteague

8% off
AU$3,554
for 7 nights, 1 home
AU$508 per night
includes taxes & fees
Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague
Front Porch
Sunroom
Kitchen / Living Room
Sunroom
Exceptional
(124 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
AU$1,893
for 7 nights, 1 home
AU$270 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Nice fireplace with 50” flatscreen tv above
Great sunset views of the bay!
Private kitchen
Exterior
Exceptional
(142 reviews)

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

Ocean City

7% off
AU$2,031
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Beach
Living area
Pool
Private kitchen
Exceptional
(55 reviews)

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

Ocean City

7% off
AU$7,664
for 7 nights, 1 apartment
AU$1,095 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Private kitchen
Property grounds
Room
Exterior
Exceptional
(105 reviews)

Huge Direct Oceanfront Townhouse with Beautiful Sunrises

Ocean City

7% off
AU$3,305
for 7 nights, 1 home
AU$472 per night
includes taxes & fees
Huge Direct Oceanfront Townhouse with Beautiful Sunrises
Interior
Open from Memorial Day weekend through Labor Day
Living area
Private kitchen
Exceptional
(128 reviews)

GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.

Ocean City

8% off
AU$4,233
for 7 nights, 1 home
AU$605 per night
includes taxes & fees
GorgeousTownhouse,Bay Views, pool, short walk to Ocean, Free WiFi, linens inc.
View of playground from back deck
Back deck off of bedroom and screened-in deck off of living room.
Dining area and living room
Screened-in deck
Exceptional
(202 reviews)

Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT

Ocean City

8% off
AU$2,223
for 7 nights, 1 home
AU$318 per night
includes taxes & fees
Gorgeous Renovated Townhouse-MUST BE OVER 25 TO RENT
Living area
Dining
Dining
Private kitchen
Exceptional
(13 reviews)

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

Ocean City

8% off
AU$4,953
for 7 nights, 1 apartment
AU$708 per night
includes taxes & fees
LAST DATES! Bay Sunset Getaway • Pool • 2BR/2BA • Free Linens
Living area
Interior
Room
Living area
Exceptional
(53 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,123
for 7 nights, 1 apartment
AU$303 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Private kitchen
View from the Kitchen and living room. Back Deck
Living area
Room
Exceptional
(29 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
AU$5,108
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
Beautiful ocean views
Kitchen with all major appliances and 2-seat breakfast bar
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Diamond Head - less than a half block to the beach and close to many OC attractions
Exceptional
(12 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,906
for 7 nights, 1 apartment
AU$272 per night
includes taxes & fees
Private Pool Steps From the Beach
MASTER BEDROOM
LIVING ROOM
LIVING ROOM
Indoor Pool
Exceptional
(94 reviews)

ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH

Ocean City

8% off
AU$3,276
for 7 nights, 1 apartment
AU$468 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Interior
view from balcony to living area
Breathtaking nighttime view from the condo
Ocean Front view of the Pyramid the most unique building on the beach
Exceptional
(101 reviews)

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

Ocean City

7% off
AU$2,400
for 7 nights, 1 apartment
AU$343 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
View from bedroom through the kitchen, to the living room and balcony
Living Room and Dining Room
Pool
Balcony Furniture
Exceptional
(44 reviews)

Moos Casa Sea Casa, beach side, private balcony, outdoor pool

Ocean City

11% off
AU$2,068
for 7 nights, 1 apartment
AU$295 per night
includes taxes & fees
Moos Casa Sea Casa, beach side, private balcony, outdoor pool
Room
Exterior
Pool
Wonderful
(67 reviews)

OCEANFRONT! 2025 Prime Weeks Available! Great Views! Covered Pool in Summer!

Ocean City

12% off
AU$3,336
for 7 nights, 1 apartment
AU$477 per night
includes taxes & fees
OCEANFRONT! 2025 Prime Weeks Available! Great Views! Covered Pool in Summer!
Interior
Exterior
Room
Bathroom
Exceptional
(89 reviews)

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

Ocean City

8% off
AU$3,555
for 7 nights, 1 apartment
AU$508 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Room
Exterior
Interior
Private kitchen
Exceptional
(9 reviews)

Broad Marsh Beach Home | Pool + Balcony Views

Ocean City

5% off
AU$3,746
for 7 nights, 1 apartment
AU$535 per night
includes taxes & fees
Broad Marsh Beach Home | Pool + Balcony Views
Exterior
Relax on a chaise in the fresh ocean air
Property grounds
You might want to sleep with the windows open...View from bdrm 1 window
Exceptional
(159 reviews)

Ocean Front Serene Coastal Views

Ocean City

7% off
AU$4,001
for 7 nights, 1 apartment
AU$572 per night
includes taxes & fees
Ocean Front Serene Coastal Views
Private kitchen
Living area
Dining
Dining
Exceptional
(53 reviews)

No need to look any further for a one bedroom in OC. Long term rates available.

Ocean City

7% off
AU$2,133
for 7 nights, 1 apartment
AU$305 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
Queen room 1 with en-suite bathroom
Living room from kitchen
Fire pit patio. You will need to bring your own wood.
Dining room and books
Exceptional
(159 reviews)

The Brass Crab - Check in/out any day!

Chincoteague

7% off
AU$2,150
for 7 nights, 1 home
AU$307 per night
includes taxes & fees
The Brass Crab - Check in/out any day!
18-1Q7A9295
07-1Q7A9356
21-1Q7A9241
Interior
Exceptional
(14 reviews)

Marigot Beachfront Condominium

Ocean City

5% off
AU$2,357
for 7 nights, 1 apartment
AU$337 per night
includes taxes & fees
Marigot Beachfront Condominium
Living room ocean view window
Balcony View
Kitchen
Heated Indoor Pool
Excellent
(100 reviews)

Spacious Ocean View Condo

Ocean City

6% off
AU$1,809
for 7 nights, 1 apartment
AU$258 per night
includes taxes & fees
Spacious Ocean View Condo
  • 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:

  • 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)
  • Bayside Resort Golf Club (29.2 mi / 47 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)
  • Maryland Beach (29 mi / 46.7 km)
  • Chincoteague National Wildlife Refuge (8 mi / 12.9 km)
  • Pocomoke River State Park (11.9 mi / 19.2 km)
  • Assateague Point (13.4 mi / 21.5 km)
  • Ocean City Inlet (20.4 mi / 32.8 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 Stayz 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 Stayz 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 Stayz, 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 Stayz'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.