Book Holiday Homes in Smith Island
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Featured Holiday Homes in Smith Island
Charming 3-bedroom house with WiFi, AC in peaceful Reedville
Cottage near the Bay
Waterfront Scotland Beach Retreat w/ Private Beach
Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10
Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier
Virginia Retreat on Wicomico River w/ Dock!
Bay House with Amazing View & Swimming Pool (open May- Sept.)
18-Acre Waterfront Sanctuary: Peace & Privacy
Waterfront Marion Station Retreat w/ Private Dock!
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 | 75 Holiday Homes |
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Lowest Price | NZ$353 |
Highest Price | NZ$491 |
Popular accommodation | Charming 3-bedroom house with WiFi, AC in peaceful Reedville, Cottage near the Bay, Waterfront Scotland Beach Retreat w/ Private Beach, Magical Sunsets and Breathtaking Views in Heathsville/Wicomico River- Sleeps 10, Pine Shore Beach House on the Chesapeake Bay w/ 170ft pier, Virginia Retreat on Wicomico River w/ Dock!, Bay House with Amazing View & Swimming Pool (open May- Sept.), 18-Acre Waterfront Sanctuary: Peace & Privacy, Waterfront Marion Station Retreat w/ Private Dock! |
More accommodations in Smith Island
Top trending hotels in Smith Island
Historic home on Smith Island w/ dock!
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Blue Anchor Cottage at Smith Island MD Quaint & Charming Beach Cottage
Deal Island Bay Cottage
More ways to explore Smith Island
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^Subject to availability and chosen travel dates.