Book Holiday Homes in Smith Island
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Smith Island

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

Cottage near the Bay

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Secluded Waterfront Home: Game Room, Private Dock, Pedal Boat, Fire pit, Kayaks!

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

'River's Edge Retreat’ with Kayaks & River Access!

Direct waterfront access to the Chesapeake Bay with pool and hottub

250 ft Private Beach & Dock- The Perfect Riverfront Family Friendly Retreat

Chesapeake Bay and Lakefront home with Private Beach
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 | 98 Holiday Homes |
---|---|
Lowest Price | AU$319 |
Highest Price | AU$559 |
Popular accommodation | Private, Waterfront, Ultra-clean, Pet friendly, Kayaks, Canoe, Firepit, more!, Cottage near the Bay, Beachy Maryland A-Frame: Steps to Chesapeake Bay!, Secluded Waterfront Home: Game Room, Private Dock, Pedal Boat, Fire pit, Kayaks!, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, 'River's Edge Retreat’ with Kayaks & River Access!, Direct waterfront access to the Chesapeake Bay with pool and hottub, 250 ft Private Beach & Dock- The Perfect Riverfront Family Friendly Retreat, Chesapeake Bay and Lakefront home with Private Beach |
Top trending hotels in Smith Island

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Historic home on Smith Island w/ dock!

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.