Book Holiday Homes in Smithtown

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 Smithtown

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

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

Syosset NY
Stay at this holiday home in Syosset. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Bethpage Black State Park Golf Course and Oyster Bay ...
Opens in a new windowModern 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

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

Ocean Bay Park NY
Stay at this holiday home in Bay Shore. Enjoy parking (surcharge), bike hire on-site and patios. Popular attractions Ocean Beach and Sunken Forest are located ...
Opens in a new window2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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

Brentwood NY
The price is NZ$291 per night from 11 May to 12 May
NZ$291
11 May - 12 May
includes taxes & fees
Stay at this holiday home in Brentwood. Enjoy free Wi-Fi, an in-room coffee maker and housekeeping. Popular attractions Brentwood State Park and Suffolk County ...
Opens in a new windowCozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Save an average of 15% on thousands of hotels when you're signed in
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

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

Ocean Beach NY
Stay at this holiday home in Bay Shore. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Ocean Beach and Sunken Forest are ...
Opens in a new windowSpacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!

Lake Grove NY
Stay at this holiday home in Lake Grove. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Smithaven Mall and AMF Centereach Lanes are located ...
Opens in a new windowSpacious Home Located Close to Stony Brook!
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

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

Northport NY
The price is NZ$1,962 per night from 12 May to 13 May
NZ$1,962
12 May - 13 May
includes taxes & fees
Stay at this beach holiday home in Northport. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Cow Harbor Park and Northport Village Park are ...
Opens in a new windowBeautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY
The price is NZ$895 per night from 11 May to 12 May
NZ$895
11 May - 12 May
includes taxes & fees
Stay at this family-friendly holiday home in Cold Spring Harbor. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their ...
Opens in a new windowCaptain's Cottage - Cold Spring Harbor Water Views
Homelike, peaceful and centrally- home located in the hamlet of Rocky  Point  NY

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

Rocky Point NY
The price is NZ$908 per night from 11 May to 12 May
NZ$908
11 May - 12 May
includes taxes & fees
Stay at this holiday home in Rocky Point. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions North Shore Beach and Shoreham Village Park ...
Opens in a new windowHomelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Stamford CT
The price is NZ$1,435 per night from 10 May to 11 May
NZ$1,435
10 May - 11 May
includes taxes & fees
Stay at this family-friendly holiday home in Stamford. Enjoy a garden, laundry facilities and patios. Popular attractions Cove Island Park and Chelsea Piers ...
Opens in a new windowStylish Beach Home near Stamford Downtown/Beach
Don't see what you're looking for?
See all available properties in Smithtown
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Inn at Jericho

2 out of 5
101 Jericho Turnpike Westbury NY
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 10 May to 11 May
NZ$201
10 May - 11 May
includes taxes & fees
Stay at this motel in Westbury. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowInn at Jericho
Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway Hauppauge NY
Fully refundableReserve now, pay when you stay
The price is NZ$244 per night from 10 May to 11 May
NZ$244
10 May - 11 May
includes taxes & fees
Stay at this golf hotel in Hauppauge. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowHyatt Regency Long Island
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
The price is NZ$236 per night from 25 May to 26 May
NZ$236
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Hauppauge. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the clean rooms in their reviews. ...
Opens in a new windowRadisson Hotel Hauppauge-Long Island
Save an average of 15% on thousands of hotels when you're signed in
East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd. East Norwich NY
The price is NZ$197 per night from 12 May to 13 May
NZ$197
12 May - 13 May
includes taxes & fees
Stay at this business-friendly hotel in East Norwich. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff and the clean ...
Opens in a new windowEast Norwich Inn
Don't see what you're looking for?
See all available properties in Smithtown
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.