Photo by Nancy Stauffer

Assateague Island holiday rentals

We found 6,471 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Assateague Island

Showing deals for:11 Dec - 18 Dec

Upstairs sunroom
Terrace/patio
Upstairs kitchen/dinete
Upstairs living room
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
AU$2,227
for 7 nights, 1 apartment
AU$318 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Dining
Beautifully decorated, comfortable, clean home
Private kitchen
Exterior
Exceptional
(161 reviews)

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

Chincoteague

7% off
AU$2,084
for 7 nights, 1 home
AU$298 per night
includes taxes & fees
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
Private kitchen
Exterior
Property grounds
Dining
Exceptional
(9 reviews)

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

Chincoteague

8% off
AU$3,548
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Bayfront Cottage-Private Lane with Ponies in the backyard - Chincoteague
Kitchen
Sunroom
Front Porch
Kitchen / Living Room
Exceptional
(127 reviews)

Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City

Berlin

7% off
AU$1,873
for 7 nights, 1 home
AU$268 per night
includes taxes & fees
Pet Friendly Near Berlin, Assateague Island Beaches and Ocean City
Room
Private kitchen
Exterior
Living area
Exceptional
(31 reviews)

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

Berlin

7% off
AU$2,916
for 7 nights, 1 home
AU$417 per night
includes taxes & fees
Newley Renovated Beach Home, Min. to Ocean City,1st FL. Master Suite, walk in
Queen room 1 with en-suite bathroom
Living room from kitchen
Living room and dining room
Dining room and books
Exceptional
(159 reviews)

The Brass Crab - Check in/out any day!

Chincoteague

7% off
AU$2,127
for 7 nights, 1 home
AU$304 per night
includes taxes & fees
The Brass Crab - Check in/out any day!
Private kitchen
Living area
Living area
Pool
Exceptional
(57 reviews)

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

Ocean City

7% off
AU$7,583
for 7 nights, 1 apartment
AU$1,083 per night
includes taxes & fees
Beautiful Beachfront 2 Level Penthouse w 2 balconies! Full Ocean Views SLEEPS 7!
Living area
Interior
Living area
Dining
Exceptional
(53 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,101
for 7 nights, 1 apartment
AU$300 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Living area
Property grounds
Dining Room
Private kitchen
Exceptional
(111 reviews)

Direct Oceanfront 3 bedroom condo perfect for family and friends with pools

Ocean City

7% off
AU$2,209
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Direct Oceanfront 3 bedroom condo perfect for family and friends with pools
Property grounds
Great sunset views of the bay!
Nice fireplace with 50” flatscreen tv above
Exterior
Exceptional
(149 reviews)

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

Ocean City

7% off
AU$2,009
for 7 nights, 1 apartment
AU$287 per night
includes taxes & fees
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
KITCHEN/DINING ROOM
CAMPGROUND POOL, OLYMPIC SIZED
OUTDOOR SPEAKERS
DECK WITH COMFORTABLE SEATING
Exceptional
(72 reviews)

Hidden Gem! Clean & Cozy and Family Friendly!

Horntown

8% off
AU$2,779
for 7 nights, 1 home
AU$397 per night
includes taxes & fees
Hidden Gem! Clean & Cozy and Family Friendly!
Indoor Pool
LIVING ROOM
LIVING ROOM
ADAGIO UNIT 207
Exceptional
(95 reviews)

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

Ocean City

8% off
AU$3,241
for 7 nights, 1 apartment
AU$463 per night
includes taxes & fees
ADAGIO#207 BEAUTIFUL 3 BED/3 BATH OCEAN BLOCK CONDO W/INDOOR POOL STEPS TO BEACH
Exterior
Super clean , fun condo to stay in
Breathtaking nighttime views!
Ocean Front balcony, great place to relax and watch the waves!
Exceptional
(112 reviews)

Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!

Ocean City

7% off
AU$2,161
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
Delightful Escape, Oceanfront 2BDR , Awesome Views, Pool, Clean!
Welcome to Diamond Head 305 - 1 bedroom, 1.5 bathroom oceanview with building pool
Kitchen with all major appliances and 2-seat breakfast bar
Beautiful ocean views
Beautiful ocean views
Exceptional
(14 reviews)

Private Pool Steps From the Beach

Ocean City

7% off
AU$1,709
for 7 nights, 1 apartment
AU$244 per night
includes taxes & fees
Private Pool Steps From the Beach
Interior
Interior
Private kitchen
Exceptional
(66 reviews)

Beachfront living near Seacrets! Don't let this memorable getaway pass you by.

Ocean City

8% off
AU$2,655
for 7 nights, 1 apartment
AU$379 per night
includes taxes & fees
Beachfront living near Seacrets! Don't let this memorable getaway pass you by.
Breathtaking nighttime view from the condo
view from balcony to living area
Ocean Front view of the Pyramid the most unique building on the beach
Relax, Have dinner, Play games, see the ocean!
Exceptional
(102 reviews)

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

Ocean City

7% off
AU$2,161
for 7 nights, 1 apartment
AU$309 per night
includes taxes & fees
Escape to The Ocean! , Ocean Front, Beautiful View, Pool!
Living area
Living area
Atrium
Kitchen
Exceptional
(105 reviews)

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

Ocean City

7% off
AU$1,726
for 7 nights, 1 apartment
AU$247 per night
includes taxes & fees
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
Room
Exterior
Living area
Private kitchen
Exceptional
(92 reviews)

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

Ocean City

8% off
AU$3,518
for 7 nights, 1 apartment
AU$503 per night
includes taxes & fees
Great Location for your vacation. Very Pet Friendly!. Close to Boardwalk/Beach.
Dining
Private kitchen
Exterior
Living area
Exceptional
(46 reviews)

V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!

Ocean City

7% off
AU$2,433
for 7 nights, 1 apartment
AU$348 per night
includes taxes & fees
V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!
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
AU$2,099
for 7 nights, 1 home
AU$300 per night
includes taxes & fees
Dorchester Drift B: Shore Nest
Property grounds
Interior
Living area
Room
Exceptional
(49 reviews)

Fantastic Bay View with romantic sunsets!

Ocean City

8% off
AU$1,623
for 7 nights, 1 apartment
AU$232 per night
includes taxes & fees
Fantastic Bay View with romantic sunsets!
Dining
Living area
Private kitchen
Dining
Exceptional
(56 reviews)

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

Ocean City

7% off
AU$2,110
for 7 nights, 1 apartment
AU$301 per night
includes taxes & fees
No need to look any further for a one bedroom in OC. Long term rates available.
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.
Private kitchen
Exceptional
(30 reviews)

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

Ocean City

6% off
AU$5,680
for 7 nights, 1 apartment
AU$811 per night
includes taxes & fees
Direct Ocean Front...In The Middle of it All!!!
Private kitchen
Pool
Interior
Room
Exceptional
(6 reviews)

2BR Condo,Pools & Walk to Beach

Ocean City

47% off
AU$1,548
for 7 nights, 1 apartment
AU$221 per night
includes taxes & fees
2BR Condo,Pools & Walk to Beach
  • 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)
  • 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 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.