Book Holiday Homes in Smithtown

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Featured Holiday Homes in Smithtown

Serene Beach Cottage Robbins Rest, Fire Island

Serene Beach Cottage Robbins Rest, Fire Island

Robbins Rest
With a stay at this vacation home in Ocean Beach, you'll be by the sea, just a 2-minute walk from Atlantique Beach and 7 minutes by foot from Great South ...
Serene Beach Cottage Robbins Rest, Fire Island
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

Bay Shore
With a stay at this vacation home in Bay Shore, you'll be within a 5-minute walk of Gilgo State Park and South Shore University Hospital.
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

Mastic
The price is AU$262 per night from 17 Aug to 18 Aug
AU$262
17 Aug - 18 Aug
includes taxes & fees
Located in Mastic, this vacation home is by the sea, within a 10-minute drive of Brookhaven National Laboratory and Carmans River.
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
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Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
The price is AU$878 per night from 6 Aug to 7 Aug
AU$878
6 Aug - 7 Aug
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 ...
Captain's Cottage - Cold Spring Harbor Water Views
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.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Amazing Rocky Point Retreat Overlooking the Sound!

Amazing Rocky Point Retreat Overlooking the Sound!

Rocky Point
Located in Rocky Point, this vacation home is by the sea, within a 5-minute drive of North Shore Beach and Clifton H. Lee Memorial Park.
Amazing Rocky Point Retreat Overlooking the Sound!
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
With a stay at this vacation home in Bay Shore, you'll be a 2-minute walk from Great South Bay and 15 minutes by foot from Ocean Beach.
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Waterfront & private beach  Scandinavian style house near Bellport, NY

Waterfront & private beach Scandinavian style house near Bellport, NY

Brookhaven
Located in Brookhaven, this vacation home is on the waterfront, a 1-minute drive from Great South Bay and 6 minutes from Carmans River.
Waterfront & private beach Scandinavian style house near Bellport, NY
Updated home in great location with spacious living & outdoor features

Updated home in great location with spacious living & outdoor features

Ocean Bay Park
When you stay at this vacation home in Ocean Beach, you'll be by the sea, within a 5-minute drive of Great South Bay and Ocean Beach.
Updated home in great location with spacious living & outdoor features
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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
509 Holiday Homes
Lowest Price
AU$194
Highest Price
AU$878
Popular accommodation
Serene Beach Cottage Robbins Rest, Fire Island, Spacious 5-bedroom house in charming Bay Shore with AC, WiFi, Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach, Captain's Cottage - Cold Spring Harbor Water Views, Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville, Amazing Rocky Point Retreat Overlooking the Sound!, Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park, Waterfront & private beach Scandinavian style house near Bellport, NY, Updated home in great location with spacious living & outdoor features

Top trending hotels in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Smithtown
The price is AU$359 per night from 31 Aug to 1 Sept
AU$359
31 Aug - 1 Sept
includes taxes & fees
With a stay at this vacation home in Smithtown, you'll be within a 10-minute drive of Stony Brook University and Nissequogue River.
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ 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.
Norwalk Inn & Conference Center
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 AU$252 per night from 17 Aug to 18 Aug
AU$252
17 Aug - 18 Aug
includes taxes & fees
Located in Hauppauge, Hyatt Regency Long Island is by the ocean, within a 5-minute drive of Hauppauge Industrial Park and Lakeland County Park.
Hyatt Regency Long Island
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Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

2.5 out of 5
2000 North Ocean Ave., Farmingville, NY
The price is AU$194 per night from 1 Sept to 2 Sept
AU$194
1 Sept - 2 Sept
includes taxes & fees
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
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See all available properties in Smithtown
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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.

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^Subject to availability and chosen travel dates.