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

Bay Front Small Contemporary

Cottage near the Bay

Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront!

Waterfront Getaway: Kayaks, Paddle Board, Fishing!

Secluded River Front Cottage

Beautiful Bayfront with Sanctuary Private Beach

Walk to Main Street: Family-Friendly Crisfield Gem

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Newly updated 3 bedroom cottage with Solo Stove fire pit
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 | 89 Holiday Homes |
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Lowest Price | NZ$319 |
Highest Price | NZ$584 |
Popular accommodation | Bay Front Small Contemporary, Cottage near the Bay, Private infinity pool, plus your own dock, kayaks, and bikes on the waterfront! , Waterfront Getaway: Kayaks, Paddle Board, Fishing!, Secluded River Front Cottage, Beautiful Bayfront with Sanctuary Private Beach , Walk to Main Street: Family-Friendly Crisfield Gem, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, Newly updated 3 bedroom cottage with Solo Stove fire pit |
More accommodations in Smith Island
Top trending hotels in Smith Island

Historic home on Smith Island w/ dock!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

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

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
More ways to explore Smith Island
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^Subject to availability and chosen travel dates.