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Holiday Homes in Assateague Island

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Our top choices for Assateague Island holiday homes

Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Bethany Beach and Close by Marinas! Family and Pet Friendly!!
Ocean View
9.2 out of 10, Wonderful, (79)
"The house and property was very spacious and comfortable. We enjoyed our stay and visit to the area very much."
United States
gisela j.
The price is €328
includes taxes & fees
22 Dec - 23 Dec
Bethany Beach and Close by Marinas! Family and Pet Friendly!!

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (23)
"Loved that it was right on the bay. "
United States
Debra
The price is €118
includes taxes & fees
29 Dec - 30 Dec
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Steps to the Beach : Sea Loft 103:

Steps to the Beach : Sea Loft 103:
North Ocean City
10.0 out of 10, Exceptional, (3)
"Too many lockboxes and under the step was a little deceiving due to finding the key on the pole right outside the door. Otherwise this was a great place and perfect location. "
United States
Kris K.
The price is €376
includes taxes & fees
27 Dec - 28 Dec
Steps to the Beach : Sea Loft 103:

OC/Fenwick Island Townhouse with Pool!

OC/Fenwick Island Townhouse with Pool!
North Ocean City
9.6 out of 10, Exceptional, (11)
"Perfect location, the house is very convenient and practical. We were 15 and slept comfortably. The host communicated quickly and answered any questions we had. "
United States
Sheyla L.
OC/Fenwick Island Townhouse with Pool!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (135)
"Very lovely pkace!! Would def book again!!"
United States
Brenda F.
The price is €270
includes taxes & fees
22 Dec - 23 Dec
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

Ocean Pines Chalet !

Ocean Pines Chalet !
Ocean Pines
9.8 out of 10, Exceptional, (10)
"Everything was wonderful. House was clean and comfortable. Perfect place for our family reunion. Would definitely book this house again! "
United States
Jenni D.
The price is €607
includes taxes & fees
22 Dec - 23 Dec
Ocean Pines Chalet !

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
Downtown Ocean City
10.0 out of 10, Exceptional, (17)
"Fantastic clean rental. Great location!"
United States
Jeremy & Karen W.
The price is €270
includes taxes & fees
28 Dec - 29 Dec
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
2.0 star property
Deep Hole
10.0 out of 10, Exceptional, (7)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
The price is €291
includes taxes & fees
27 Dec - 28 Dec
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk
2.0 star property
Downtown Ocean City
10.0 out of 10, Exceptional, (1)
"Great place to stay!"
United States
Joseph D.
The price is €267
includes taxes & fees
5 Jan - 6 Jan 2026
BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

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

DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15
North Ocean City
9.8 out of 10, Exceptional, (143)
"The property had everything we needed. The owner was easy to communicate with."
United States
Thomas R.
The price is €406
includes taxes & fees
27 Dec - 28 Dec
DownByTheBay-115 WATERFRONT! 4 BR/3.5BA at Broad Marsh OC with GARAGE Sleeps 15

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Accomac
10.0 out of 10, Exceptional, (26)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is €278
includes taxes & fees
22 Dec - 23 Dec
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (59)
"The Property was very well-maintained and accommodating, with most everything you could need. This made the stay much simpler and more enjoyable. The dock and kayaks were a great addition to the fun. "
United States
Randy A.
The price is €380
includes taxes & fees
22 Dec - 23 Dec
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

3 BR End Unit Rowhouse 1 Mile to Bethany Boardwalk, Walk to Shops & Restaurants

3 BR End Unit Rowhouse 1 Mile to Bethany Boardwalk, Walk to Shops & Restaurants
Bethany Beach
9.8 out of 10, Exceptional, (9)
"Scott was very nice and communicative. The inside was clean and provided a home away from home. "
United States
Kimberley Y.
The price is €246
includes taxes & fees
23 Dec - 24 Dec
3 BR End Unit Rowhouse 1 Mile to Bethany Boardwalk, Walk to Shops & Restaurants

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

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (66)
"Great location. The house was perfect for our family. I especially enjoyed the swing on the porch "
United States
pat B.
The price is €234
includes taxes & fees
22 Dec - 23 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Ocean Pines
10.0 out of 10, Exceptional, (37)
"Nice location in quiet neighborhood. Tastefully decorated. Well maintained and equipped."
United States
Natale M.
The price is €330
includes taxes & fees
26 Dec - 27 Dec
Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Beach Paradise 105 - Beach Home at Broad Marsh OC

Beach Paradise 105 - Beach Home at Broad Marsh OC
North Ocean City
9.8 out of 10, Exceptional, (9)
"Beautiful property, great location, and very clean! We all enjoyed our stay and hope to be back!"
United States
Conor K.
The price is €265
includes taxes & fees
4 Jan - 5 Jan 2026
Beach Paradise 105 - Beach Home at Broad Marsh OC

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (3)
"Wonderful stay at beautiful homeamazingly"
United States
Jonathan D.
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is €351
includes taxes & fees
22 Dec - 23 Dec
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Tahitian Sunrise Retreat

Tahitian Sunrise Retreat
North Ocean City
The price is €438
includes taxes & fees
2 Jan - 3 Jan 2026
Tahitian Sunrise Retreat

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
2.0 star property
Snow Hill
10.0 out of 10, Exceptional, (2)
"The hosts were wonderful, the house is beautiful, access & location was perfect. Next time I'm in the area & this place is avaliable, this is where I want to stay again. I recommend this house if you're in the area!!!Thanks to The Smiths"
United States
Sadat J.
The price is €183
includes taxes & fees
3 Jan - 4 Jan 2026
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
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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