Holiday Homes in Assateague Island

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Featured Holiday Homes in Assateague Island

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (101)
"We loved staying in the floating bungalows- what a cool experience! "
Blufin Bungalows & Marina

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (44)
"Enjoyed staying at the place with some friends and colleagues— the place was clean and cutely decorated. The bikes were nice and wish we had time for the kayaks but we were working for part of the weekend! Thanks for the stay ! Cheers!"
The price is NZ$475
includes taxes & fees
30 Apr - 1 May
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

The purple door at the bay.

9.4 out of 10, Exceptional, (40)
"We loved the view and can not wait to go back!"
The price is NZ$785
includes taxes & fees
5 May - 6 May
The purple door at the bay.

PRICE DROP - HIGHLY RATED! Cozy, single family home close to beach and golf

10.0 out of 10, Exceptional, (23)
"This is a beautiful home close to everything but still a quiet neighborhood. I was disappointed that I was there during the winter this house would only get better as the weather gets better. great communication with the owner and would love to stay again"
PRICE DROP - HIGHLY RATED! Cozy, single family home close to beach and golf

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (23)
"Our condo had it all; space, kitchen equipment, unbelievable views, and most of all a comfortable bed. The owner thought of everything to make our 4 day stay perfect."
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Large 5 BR 4 BA Home is Ready for Family Fun!

10.0 out of 10, Exceptional, (6)
"Property was well maintained and very spacious. Would definitely return if in the area again."
Large 5 BR 4 BA Home is Ready for Family Fun!

Fabulous Fenwick Island! Waterfront property, charming, chic!

10.0 out of 10, Exceptional, (189)
"This was our first family vacation together in a long time (11 years). The house was beautiful and right on the water. It was well stocked, dog friendly and very clean. We brought three dogs who enjoyed the fenced in yard and neighborhood walks. One of the dog’s leash broke and right there in laundry room was an extra leash which we used until we could get a new one. I didn’t sleep in all the beds but the bed in the main bedroom was so comfortable. Everyone said the house was a good find...
Fabulous Fenwick Island! Waterfront property, charming, chic!

Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

9.8 out of 10, Exceptional, (79)
"Excellent.communication with property manager. The house was beautiful with plenty of space for our group of 8."
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!

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

9.8 out of 10, Exceptional, (128)
"Plenty of bedrooms for accomodations. Great location on the island. Host provided everything needed for a comfortable stay."
The price is NZ$1,671
includes taxes & fees
14 May - 15 May
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

5BR OceanView O/D Space/Movies, Pool, Bikes, Gear

9.6 out of 10, Exceptional, (27)
"The house was very nice, loaded with every thing needed for a pleasant stay. the kitchen had every appliance, silverware, gadget. The house was comfortable and decorated tastefully. The location was fabulous. The host was very attentive. It was an extremely pleasant stay. "
5BR OceanView O/D Space/Movies, Pool, Bikes, Gear

Beautiful and Spacious 5 Bed Townhome, end unit, located in the Bear Trap Dunes Community! Game Room, WIFI, Pools, Shuttle to the Beach, and more!

8.6 out of 10, Excellent, (4)
"Lovely rental;specious and spotless. Very accommodating property for a large varying age group. Clean packaged linens were provided. All of the appliances were in working order. We would love to return in the future."
Beautiful and Spacious 5 Bed Townhome, end unit, located in the Bear Trap Dunes Community! Game Room, WIFI, Pools, Shuttle to the Beach, and more!

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.4 out of 10, Exceptional, (32)
"Very nice property…one of the best. The host was very responsive and kind ! We are coming back this summer and hoping we can get this property again ! "
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

WATERFRONT Bethany Lakes, POOL, Pickleball,Fishing, Gym, screen porch,dogs ok!

9.6 out of 10, Exceptional, (70)
"This home is very spacious, clean beautifully furnished and in a great location. "
WATERFRONT Bethany Lakes, POOL, Pickleball,Fishing, Gym, screen porch,dogs ok!

Town of Ocean View pet friendly house with a private pool!

10.0 out of 10, Exceptional, (1)
"Absolutely loved this house. There is a ton of space for a family to spread out. Beware, there are steps everywhere. The only issue we really had was with the dryer, it did not get hot. Hopefully that will be addressed before the next group checks in. The home looks just as pictured. We hope anyone else that books this house enjoys it as much as we did.want to consider somewhere else. "
Town of Ocean View pet friendly house with a private pool!

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (49)
"Nice long weekend spent with a couple of ladies that have been friends for 40 years. The weather wasn't great, so we didn't get to enjoy the decks and outdoor seating, but the house was so comfortable and the views are so nice from those big windows in the living room, that we didn't care. The house was well stocked with towels and paper products. Loved the teas that were available and one of my friends appreciated the coffee beans. This is definitely a property that we will book again! "
The price is NZ$684
includes taxes & fees
23 Apr - 24 Apr
Stunning waterfront panoramic view getaway house

Unit 1 South - End Unit Ocean Block Townhome

8.4 out of 10, Very good, (45)
"We were in OC for the Country Calling concert, the location was great for us. Walking distance to Bad Monkey and Fagers Island was a plus! The host was very prompt in responding. "
Unit 1 South - End Unit Ocean Block Townhome

Canal Front Home w/ Dock & Fence. 5 Min walk to the beach! Pet Friendly w/fee

9.6 out of 10, Exceptional, (118)
"The screened in outdoor area was exceptionally nice. Our dog enjoyed hanging out in the cooler weather out there. Very nice location that's just a short walk away from the beach."
Canal Front Home w/ Dock & Fence. 5 Min walk to the beach! Pet Friendly w/fee

Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS

9.6 out of 10, Exceptional, (30)
"Great location"
Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS

Relaxing Breezy Seaside Retreat 3bd/2ba/2decks King Bed

10.0 out of 10, Exceptional, (23)
"Located almost right in the middle of the boardwalk. Perfect location. Perfect view and well kept house. Exactly as pictured. It was a very relaxing week and hope to get back there someday!"
Relaxing Breezy Seaside Retreat 3bd/2ba/2decks King Bed

Northside Park condo w/ Pool and Beach Supplies

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay. Located right beside North Side Park with playground and much more. Kitchen was well stocked with things you need. If traveling with kids make sure to bring paper or plastic dishes for for them. I did bring my crock pot to make pulled pork while down at the beach. There is none in the kitchen. Plenty of hot water for showers.We would definitely stay here again."
Northside Park condo w/ Pool and Beach Supplies
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.
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Other property types in Assateague Island

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (101)
"We loved staying in the floating bungalows- what a cool experience! "
Blufin Bungalows & Marina

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
The price is NZ$136
includes taxes & fees
19 May - 20 May
Majestic Hotel & Apartments

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (353)
"The property is great overall and Susette at reception was excellent. However, we were disappointed with the town itself. I guess our expectations were too high before coming here. We were expecting a more quaint small town vibe like St. Michael or Annapolis for example, with quaint small boutiques shops and great dining. "
The price is NZ$335
includes taxes & fees
23 Apr - 24 Apr
Key West Cottages
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.