Book Holiday Homes in Smithtown

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Featured Holiday Homes in Smithtown

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Seaview
With a stay at this vacation home in Ocean Beach, you'll be by the sea, just a 5-minute walk from Ocean Beach and 15 minutes by foot from Great South Bay.
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
The price is AU$734 per night from 8 Apr to 9 Apr
AU$734
includes taxes & fees
8 Apr - 9 Apr
With a stay at this vacation home, you'll be centrally located in Cold Spring Harbor, just a 3-minute walk from Cold Spring Harbor Fish Hatchery & Aquarium and ...
Captain's Cottage - Cold Spring Harbor Water Views
🌞New Listing!! Ocean View Retreat!🌞

🌞New Listing!! Ocean View Retreat!🌞

Ocean Beach
A stay at this vacation home places you in the heart of Ocean Beach, steps from Atlantique Beach and 10 minutes by foot from Ocean Beach.
🌞New Listing!! Ocean View Retreat!🌞
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Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
Cheerful 4 bedrooms residential house.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

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

Centereach
With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Luxury and Affordable Family Home

Luxury and Affordable Family Home

Wyandanch
The price is AU$1,201 per night from 7 Apr to 8 Apr
AU$1,201
includes taxes & fees
7 Apr - 8 Apr
With a stay at this vacation home in Wyandanch, you'll be within a 15-minute drive of Bethpage Black State Park Golf Course and Belmont Lake State Park.
Luxury and Affordable Family Home
Home away from home

Home away from home

West Babylon
With a stay at this vacation home in West Babylon, you'll be within a 15-minute drive of Bethpage Black State Park Golf Course and Belmont Lake State Park.
Home away from home
The Raabbit Hole

The Raabbit Hole

Ocean Beach
With a stay at this vacation home in Ocean Beach, you'll be near the beach, just a 4-minute walk from Great South Bay and 6 minutes by foot from Ocean ...
The Raabbit Hole
Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

Mastic
Located in Mastic, this vacation home is by the ocean, a 4-minute drive from Carmans River and 5 minutes from Moriches Bay.
Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.
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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
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.

Top trending hotels in Smithtown

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 7 Apr to 8 Apr
AU$188
includes taxes & fees
7 Apr - 8 Apr
Located in Farmingville, Hampton Inn Long Island-Brookhaven is connected to a shopping center, a 5-minute drive from Boomers! Medford and 6 minutes from Town ...
Hampton Inn Long Island-Brookhaven
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 AU$207 per night from 6 Apr to 7 Apr
AU$207
includes taxes & fees
6 Apr - 7 Apr
Located in Hauppauge, Radisson Hotel Hauppauge-Long Island is in the suburbs, a 1-minute drive from Hauppauge Industrial Park and 8 minutes from Sunken Meadow ...
Radisson Hotel Hauppauge-Long Island
Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

4 out of 5
3998 Brush Hollow Rd, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is AU$257 per night from 20 Apr to 21 Apr
AU$257
includes taxes & fees
20 Apr - 21 Apr
When you stay at Viana Hotel and Spa, Trademark Collection by Wyndham in Westbury, you'll be in the business district, within a 10-minute drive of Roosevelt ...
Viana Hotel and Spa, Trademark Collection by Wyndham
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East Norwich Inn

East Norwich Inn

2.5 out of 5
6321 Northern Blvd., East Norwich, NY
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 13 Apr to 14 Apr
AU$179
includes taxes & fees
13 Apr - 14 Apr
Located in East Norwich, East Norwich Inn is in the historical district, within a 10-minute drive of Cold Spring Harbor Laboratory and Tilles Center for the ...
East Norwich Inn
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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.