Book Holiday Homes in Smithtown

Start date: Check-in selected.
To Date
End date: Check-out

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

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
The price is AU$255 per night from 12 Nov to 13 Nov
AU$255
12 Nov - 13 Nov
includes taxes & fees
Located in Brentwood, this vacation home is within a 5-minute drive of Hauppauge Industrial Park and Nissequogue River.
Opens in a new windowCozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Your Quiet Home Away from Home – 3BR Oasis with  Amenities

Your Quiet Home Away from Home – 3BR Oasis with Amenities

Hauppauge, NY
With a stay at this vacation home in Hauppauge, you'll be within a 15-minute drive of Stony Brook University and Hauppauge Industrial Park.
Opens in a new windowYour Quiet Home Away from Home – 3BR Oasis with Amenities
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Bayport
When you stay at this vacation home in Bayport, you'll be on the beach, within a 5-minute drive of Great South Bay and Oak Road Beach.
Opens in a new windowLuxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Save an average of 15% on thousands of hotels when you're signed in
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
The price is AU$724 per night from 12 Nov to 13 Nov
AU$724
12 Nov - 13 Nov
includes taxes & fees
A stay at this vacation home places you in the heart of Cold Spring Harbor, within a 15-minute walk of Cold Spring Harbor State Park and Cold Spring Harbor Whaling ...
Opens in a new windowCaptain's Cottage - Cold Spring Harbor Water Views
Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!

Lake Grove
The price is AU$1,141 per night from 21 Nov to 22 Nov
AU$1,141
21 Nov - 22 Nov
includes taxes & fees
With a stay at this vacation home in Lake Grove, you'll be within a 10-minute drive of Stony Brook University and Smithaven Mall.
Opens in a new windowSpacious Home Located Close to Stony Brook!
Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University

2 out of 5
Stony Brook, NY
The price is AU$358 per night from 16 Nov to 17 Nov
AU$358
16 Nov - 17 Nov
includes taxes & fees
With a stay at this vacation home in Stony Brook, you'll be steps from Stony Brook University and a 4-minute drive from Long Island Museum of American Art, History, ...
Opens in a new windowNewly renovated Private bedroom near Stony Brook University
Stay at Black Rock Harbor

Stay at Black Rock Harbor

Bridgeport
Located in Bridgeport (Black Rock Historic District), this vacation home is within a 5-minute drive of Longfellow Park and Fairfield Medicine.
Opens in a new windowStay at Black Rock Harbor
Newly Renovated Luxury Beach House Ocean Bay Park

Newly Renovated Luxury Beach House Ocean Bay Park

Ocean Beach
When you stay at this vacation home in Bay Shore, you'll be near the beach, within a 10-minute walk of Great South Bay and Ocean Beach.
Opens in a new windowNewly Renovated Luxury Beach House Ocean Bay Park
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
A stay at this vacation home places you in the heart of Huntington, within a 5-minute drive of Huntington Hospital and Heckscher Museum of Art.
Opens in a new windowAdorable Cottage with Water Views, Across the street from Prime & other eateries
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
544 Holiday Homes
Lowest Price
AU$183
Highest Price
AU$1,141
Popular accommodation
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , Your Quiet Home Away from Home – 3BR Oasis with Amenities, Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville, Captain's Cottage - Cold Spring Harbor Water Views, Spacious Home Located Close to Stony Brook!, Newly renovated Private bedroom near Stony Brook University, Stay at Black Rock Harbor, Newly Renovated Luxury Beach House Ocean Bay Park, Adorable Cottage with Water Views, Across the street from Prime & other eateries

Top trending hotels in Smithtown

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
A stay at Norwalk Inn & Conference Center places you in the heart of Norwalk, within a 5-minute drive of Historic South Norwalk and The SoNo Collection.
Opens in a new windowNorwalk Inn & Conference Center
Hilton Garden Inn Westbury

Hilton Garden Inn Westbury

3 out of 5
1575 Privado Rd, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is AU$204 per night from 23 Nov to 24 Nov
AU$204
23 Nov - 24 Nov
includes taxes & fees
When you stay at Hilton Garden Inn Westbury in Westbury, you'll be in a shopping district, within a 5-minute drive of Roosevelt Field Mall and Nassau Veterans ...
Opens in a new windowHilton Garden Inn Westbury
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 AU$183 per night from 12 Nov to 13 Nov
AU$183
12 Nov - 13 Nov
includes taxes & fees
With a stay at Inn at Jericho in Westbury, you'll be within a 10-minute drive of Roosevelt Field Mall and Nassau Veterans Memorial Coliseum.
Opens in a new windowInn at Jericho
Save an average of 15% on thousands of hotels when you're signed in
 Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S, Hauppauge, NY
Fully refundable
The price is AU$227 per night from 7 Dec to 8 Dec
AU$227
7 Dec - 8 Dec
includes taxes & fees
Located in Hauppauge, Holiday Inn Express Hauppauge-Long Island is a 2-minute drive from Hauppauge Industrial Park and 7 minutes from SUSA Orlin & Cohen Sports ...
Opens in a new window Holiday Inn Express Hauppauge-Long Island
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.