Book Holiday Homes in Smith Island
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Featured Holiday Homes in Smith Island

Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!

Waterfront 5BR Getaway with AC, Private Dock & Scenic Heathsville Views

Cottage near the Bay

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10

Spacious Gorgeous Waterfront Home With Sunset View

Newly updated 3 bedroom cottage with Solo Stove fire pit

BayWatch: Chesapeake Bayfront Retreat with a Small Private Beach. Dog Friendly.
Smith Island Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Smith Island vacation homes are the perfect way for you to wing it.
Holiday houses in Smith Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Smith Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Smith Island adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Smith Island with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Smith Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Smith Island Holiday Homes essential information
Accommodation | 77 Holiday Homes |
|---|---|
Lowest Price | AU$136 |
Highest Price | AU$441 |
Popular accommodation | Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!, Waterfront 5BR Getaway with AC, Private Dock & Scenic Heathsville Views, Cottage near the Bay, FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS, Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Spacious Gorgeous Waterfront Home With Sunset View, Newly updated 3 bedroom cottage with Solo Stove fire pit, BayWatch: Chesapeake Bayfront Retreat with a Small Private Beach. Dog Friendly. |
Top trending hotels in Smith Island

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Spacious 5-bedroom house with WiFi, AC and private dock on charming Smith Island

Historic home on Smith Island w/ dock!

Rodeway Inn at Somers Cove Marina
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^Subject to availability and chosen travel dates.
