Holiday Homes in Smithtown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Smithtown holiday homes

1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in Brentwood

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.4 out of 10, Exceptional, (37 reviews)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is €135
includes taxes & fees
23 Jan - 24 Jan
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Dining

Holiday Home in Shirley

3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is €528
includes taxes & fees
25 Jan - 26 Jan
3 Story Beach Waterview, 3 KING bed, golf putting green!
Marina

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (74 reviews)
"Location was perfect!"
United States
Linda J P.
The price is €402
includes taxes & fees
25 Jan - 26 Jan
Captain's Cottage - Cold Spring Harbor Water Views
Dining

Holiday Home in Historic District

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
10.0 out of 10, Exceptional, (9 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is €433
includes taxes & fees
5 Feb - 6 Feb
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Coffee/tea maker, spices

Holiday Home in Huntington

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, modern and comfortable. Host was helpful and a great communicator. We will definitely stay again! "
United States
Tricia H.
The price is €343
includes taxes & fees
18 Feb - 19 Feb
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Dining

Holiday Home in East Patchogue

Pure Paradise Hamptons Getaway
10.0 out of 10, Exceptional, (1 review)
"Nice house and great pool. "
United States
Bret C.
The price is €1,730
includes taxes & fees
26 Jan - 27 Jan
Pure Paradise Hamptons Getaway
2 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Stony Brook

Stylish 2BR House Near Stony Brook University and shopping, fully renovated
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"The house was cozy and the host was excellent."
United States
Kim G.
The price is €603
includes taxes & fees
4 Feb - 5 Feb
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Smart TV, books

Holiday Home in Rocky Point

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is €460
includes taxes & fees
4 Feb - 5 Feb
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Pool

Holiday Home in Glen Head

2-bedroom house in pleasant Glen Head with AC and charm
2.0 star property
The price is €367
includes taxes & fees
23 Jan - 24 Jan
2-bedroom house in pleasant Glen Head with AC and charm
Private kitchen

Holiday Home in Westbury

Modern and spacious house close to NYC / Garden City
10.0 out of 10, Exceptional, (1 review)
"I had a wonderful stay at Nishant's home. Nishant was incredibly responsive, respectful, and helpful throughout my visit. The home was spotless, very comfortable, and easy to access, which made my stay even more enjoyable. I would highly recommend staying here for a pleasant and hassle-free experience."
United States
Rohan N.
Modern and spacious house close to NYC / Garden City
Property grounds

Holiday Home in Shirley

Waterfront Designer Retreat. Stunning Sunsets & Fire Pit. 5 Minutes to the Beach
Waterfront Designer Retreat. Stunning Sunsets & Fire Pit. 5 Minutes to the Beach
Property grounds

Holiday Home in Saint James

The Bella Vista St James! Waterfront house with a beach dock and so much more!
10.0 out of 10, Exceptional, (1 review)
"This property is beautiful and the host was very responsive. We were in town for a funeral so unfortunately wasnt able to enjoy the house as much as I would have liked to. The view is breathtaking, we saw deer, wild turkeys, swans and more. I would suggest kids 8 would be better suited. I had to chase my little around to ensure they weren't touching or playing with any of the decorations. Plenty of bathrooms and counter space. No cell reception but the Wi-Fi worked throughout the whole home....
United States
Devin k.
The price is €1,765
includes taxes & fees
25 Jan - 26 Jan
The Bella Vista St James! Waterfront house with a beach dock and so much more!
Dining

Holiday Home in Stony Brook

Modern 1 bedroom apartment near Stony Brook university hospital walking distance
10.0 out of 10, Exceptional, (1 review)
"There was a slight hiccup but it was resolved in a prompt timely manner. I appreciate the host and her accommodating me when a problem came up. I will definitely stay at one of her properties again. Thank you!"
United States
Margaret A.
The price is €533
includes taxes & fees
1 Feb - 2 Feb
Modern 1 bedroom apartment near Stony Brook university hospital walking distance
Dining

Holiday Home in Old Bethpage

Abundant space with a full kitchen next to trails and golfing
2.0 star property
The price is €293
includes taxes & fees
25 Jan - 26 Jan
Abundant space with a full kitchen next to trails and golfing
Smart TV

Holiday Home in Lake Grove

Spacious Home Located Close to Stony Brook!
7.6 out of 10, Good, (26 reviews)
"Heeat location and nice clean property. Would recommend and stay again "
United States
HUGH G.
The price is €693
includes taxes & fees
6 Feb - 7 Feb
Spacious Home Located Close to Stony Brook!
Smart TV

Holiday Home in Hicksville

Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema
9.2 out of 10, Wonderful, (5 reviews)
The price is €431
includes taxes & fees
26 Jan - 27 Jan
Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema
Fridge, microwave, oven, stovetop

Holiday Home in Huntington

Charming 3-bedroom modern family retreat!
9.6 out of 10, Exceptional, (9 reviews)
"Great location & thoughtful amenities."
United States
Joshua
The price is €521
includes taxes & fees
26 Jan - 27 Jan
Charming 3-bedroom modern family retreat!
Dining

Holiday Home in Stony Brook

3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
6.0 out of 10, (2 reviews)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
The price is €519
includes taxes & fees
24 Jan - 25 Jan
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
TV

Holiday Home in North Babylon

Family-Friendly 4BR - Near Parks, Golf & Beaches
2.0 star property
The price is €445
includes taxes & fees
23 Jan - 24 Jan
Family-Friendly 4BR - Near Parks, Golf & Beaches
Private kitchen

Holiday Home in Brookhaven

4-bedroom house in awesome Brookhaven with AC
The price is €570
includes taxes & fees
23 Jan - 24 Jan
4-bedroom house in awesome Brookhaven with AC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Smithtown Hotel Reviews

SureStay Plus by Best Western Woodbury Inn

SureStay Plus by Best Western Woodbury Inn

10/10 Excellent
"The staff was very nice & accommodating, breakfast was good & my room was clean. I would definitely recommend this hotel to others. "
David 3-night trip
Posted 2 days ago
SureStay Plus by Best Western Woodbury Inn

Find out more about Smithtown

Smithtown Holiday Homes information

Number of reviews
214
Accommodation
516 Holiday Homes
Lowest Price
€135
Highest Price
€1,765