Book Holiday Homes in Smithtown
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Featured Holiday Homes in Smithtown

Modern 5BR Home W/Private Backyard Basket Ball Hoop Near NY& Long Island Beaches

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious Home Located Close to Stony Brook!

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Captain's Cottage - Cold Spring Harbor Water Views

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Stylish Beach Home near Stamford Downtown/Beach
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 | 516 Holiday Homes |
|---|---|
Lowest Price | NZ$197 |
Highest Price | NZ$1,962 |
Popular accommodation | Modern 5BR Home W/Private Backyard Basket Ball Hoop Near NY& Long Island Beaches, 2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment, Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park, Spacious Home Located Close to Stony Brook!, Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC, Captain's Cottage - Cold Spring Harbor Water Views, Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY, Stylish Beach Home near Stamford Downtown/Beach |
Top trending hotels in Smithtown

Inn at Jericho

Hyatt Regency Long Island

Radisson Hotel Hauppauge-Long Island

East Norwich Inn
More ways to explore Smithtown
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
