Holiday Homes in Assateague Island

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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Featured Holiday Homes in Assateague Island

Blufin Bungalows & Marina
On the beach

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (87)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (37)
"We stayed for 3 nights in this comfortable home. Plenty of space for all 5 of us (4 adults and 1 teen) to cook easy breakfasts, lunches, and bake cookies, play board games, as well as a great home base for walking to restaurants, shopping, and heading out for nature walks, boat tours. We very much enjoyed our stay. Easy communication with owners, too. "
The price is NZ$507
includes taxes & fees
3 Apr - 4 Apr
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
The purple door at the bay.
Beach nearby

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$834
includes taxes & fees
2 Apr - 3 Apr
The purple door at the bay.
PRICE DROP - HIGHLY RATED! Cozy, single family home close to beach and golf
Beach

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

10.0 out of 10, Exceptional, (22)
"Very clean"
PRICE DROP - HIGHLY RATED! Cozy, single family home close to beach and golf
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
On the beach

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

10.0 out of 10, Exceptional, (22)
"We had a great time, the condo is lovely has great views, lots of space. The entire process from booking to checkout was a breeze! "
PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Large 5 BR 4 BA Home is Ready for Family Fun!
Fridge, microwave, oven, stovetop

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!
Outdoor dining

Fabulous Fenwick Island! Waterfront property, charming, chic!

10.0 out of 10, Exceptional, (187)
"The house was great. Clean and big enough for the group. Close to golfing and anything else we needed. Perfect place. "
Fabulous Fenwick Island! Waterfront property, charming, chic!
Absolutely Stunning 5 BR 5 BA Canal Front Home - You'll Never Want to Leave!
Exterior detail

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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (126)
"This was perfect for our group of friends and the hosts were very accommodating! "
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
5BR OceanView O/D Space/Movies, Pool, Bikes, Gear
Property grounds

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!
Pool

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⭐️
Property grounds

⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️

9.6 out of 10, Exceptional, (29)
"Fantastic weekend at the beach watching football playoffs with the most beautiful woman in the world. Only issue was dead batteries in all the remotes. Quickly rectified by management "
⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️
WATERFRONT Bethany Lakes, POOL, Pickleball,Fishing, Gym, screen porch,dogs ok!
Sun-loungers

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!
Hair dryer, towels

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

"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
Property grounds

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (48)
"We couldn't be happier with our experience with Nick and our stay at his beautiful unique home! It was peaceful, relaxing, and had the most amazing views from the main living area! My whole family was sad to leave!! "
The price is NZ$994
includes taxes & fees
10 Apr - 11 Apr
Stunning waterfront panoramic view getaway house
Unit 1 South - End Unit Ocean Block Townhome
Interior

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
Terrace/patio

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

9.6 out of 10, Exceptional, (115)
" Area was amazing house is simply adorable! Quiet neighborhood -Great views and outdoor is so relaxing!Hope to visit again soon! The town of Bethany is adorable right in between the hustle and bustle of area beaches."
Canal Front Home w/ Dock & Fence. 5 Min walk to the beach! Pet Friendly w/fee
Some Avail for 2025 Mid Town Ocean City on 69th St Townhome
Exterior

Some Avail for 2025 Mid Town Ocean City on 69th St Townhome

9.6 out of 10, Exceptional, (56)
"This was our second time staying here. The place is a perfect spot- close to the beach, bars, restaurants and mini golf. Owners are very responsive. We look forward to retuning next year!!!"
Some Avail for 2025 Mid Town Ocean City on 69th St Townhome
Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS
Terrace/patio

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
Outdoor dining

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

10.0 out of 10, Exceptional, (21)
"This was a quick getaway for me and my kids but the house provided us with the R&R we needed. Location was wonderful being on the quiet end of the OC boardwalk. House was clean and had everything we needed. We enjoyed playing Ocean City Monopoly! Views of the beach were fantastic. We would love to stay here again."
Relaxing Breezy Seaside Retreat 3bd/2ba/2decks King Bed
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

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (338)
"Property was very clean and very comfortable "
The price is NZ$280
includes taxes & fees
8 Apr - 9 Apr
Key West Cottages
Shore Point Cottages
Deluxe Cottage | Private kitchen

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (204)
"I love how quiet the place is. It gives you a remote feeling. A very nice getaway!"
Shore Point Cottages
Majestic Hotel & Apartments
Basic Apartment, 2 Bedrooms, Non Smoking | Private kitchen

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
Majestic Hotel & Apartments
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.