Book Holiday Homes in Smithtown
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Featured Holiday Homes in Smithtown

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Captain's Cottage - Cold Spring Harbor Water Views

🌞New Listing!! Ocean View Retreat!🌞

Cheerful 4 bedrooms residential house.

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Luxury and Affordable Family Home

Home away from home

The Raabbit Hole

Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.
Smithtown 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 Smithtown vacation homes are the perfect way for you to wing it.
Holiday houses in Smithtown 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 Smithtown 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 Smithtown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Smithtown 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 Smithtown 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.
Smithtown Holiday Homes essential information
Accommodation | 471 Holiday Homes |
---|---|
Lowest Price | AU$179 |
Highest Price | AU$1,201 |
Popular accommodation | Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms, Captain's Cottage - Cold Spring Harbor Water Views, 🌞New Listing!! Ocean View Retreat!🌞, Cheerful 4 bedrooms residential house., Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Luxury and Affordable Family Home, Home away from home , The Raabbit Hole, Hottub, ⛳️,firepits, heated pool, pool table, Basketball court. |
Holiday Homes in Smithtown
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Top trending hotels in Smithtown

Hampton Inn Long Island-Brookhaven

Radisson Hotel Hauppauge-Long Island

Viana Hotel and Spa, Trademark Collection by Wyndham

East Norwich Inn
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Top picks
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^Subject to availability and chosen travel dates.