Holiday Homes in Smithtown

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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured Holiday Homes in Smithtown

Terrace/patio
The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma

2.0 star property
Ronkonkoma
10.0 out of 10, Exceptional, (4)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$462
includes taxes & fees
15 Dec - 16 Dec
The Royal Suite - Ronkonkoma
Property grounds
3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!

Shirley
10.0 out of 10, Exceptional, (21)
"The place was very well sized and in a lovely location by the beach. Eddie was extremely responsive to all of our questions through out our stay. Would highly recommend!"
United States
Matt H.
The price is AU$958
includes taxes & fees
3 Dec - 4 Dec
3 Story Beach Waterview, 3 KING bed, golf putting green!
1 bedroom, WiFi, bed sheets
Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University

2.0 star property
Stony Brook
8.0 out of 10, Very good, (2)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is AU$376
includes taxes & fees
7 Dec - 8 Dec
Newly renovated Private bedroom near Stony Brook University
1 bedroom, iron/ironing board, free WiFi, bed sheets
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
9.6 out of 10, Exceptional, (35)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is AU$255
includes taxes & fees
4 Dec - 5 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Microwave, oven, stovetop, coffee/tea maker
Peaceful private 2-bedroom house in Bayport.Amazing location!

Peaceful private 2-bedroom house in Bayport.Amazing location!

2.0 star property
Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is AU$432
includes taxes & fees
4 Dec - 5 Dec
Peaceful private 2-bedroom house in Bayport.Amazing location!
Beach
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Mastic Beach
10.0 out of 10, Exceptional, (5)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
United States
Leonid T.
The price is AU$509
includes taxes & fees
8 Dec - 9 Dec
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Smart TV, fireplace, ping pong, computer monitors
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AU$725
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views
2 bedrooms, iron/ironing board, WiFi, bed sheets
Stylish 2BR House Near Stony Brook University and shopping, fully renovated

Stylish 2BR House Near Stony Brook University and shopping, fully renovated

2.0 star property
Stony Brook
10.0 out of 10, Exceptional, (1)
"perfect place"
New Zealand
Akaki G.
The price is AU$822
includes taxes & fees
3 Dec - 4 Dec
Stylish 2BR House Near Stony Brook University and shopping, fully renovated
Coffee/tea maker, spices
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Huntington
10.0 out of 10, Exceptional, (5)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
United States
Patrick
The price is AU$611
includes taxes & fees
1 Jan - 2 Jan 2026
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Exterior
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
Norwalk
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
The price is AU$1,030
includes taxes & fees
15 Dec - 16 Dec
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Outdoor spa tub
Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball

Mastic
10.0 out of 10, Exceptional, (27)
"Stayed here for my wedding weekends and absolutely loved the house! Very spacious and beautiful yard! Had so much fun "
United States
Tiffany I.
The price is AU$1,924
includes taxes & fees
3 Dec - 4 Dec
Hottub, ⛳️, htd pool, Sauna, Basketball
Microwave
CHOICE HOME 3-BEDROOM HOUSE -in the heart of West Babylon, NY

CHOICE HOME 3-BEDROOM HOUSE -in the heart of West Babylon, NY

2.0 star property
West Babylon
8.0 out of 10, Very good, (1)
"A safe and quiet place to sleep. "
United States
Yves F.
CHOICE HOME 3-BEDROOM HOUSE -in the heart of West Babylon, NY
Outdoor pool
Pure Paradise Hamptons Getaway

Pure Paradise Hamptons Getaway

East Patchogue
10.0 out of 10, Exceptional, (1)
"Nice house and great pool. "
United States
Bret C.
The price is AU$4,135
includes taxes & fees
4 Dec - 5 Dec
Pure Paradise Hamptons Getaway
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
The price is AU$836
includes taxes & fees
1 Jan - 2 Jan 2026
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Property grounds
Choice home welcome to the highest rated home on every platform

Choice home welcome to the highest rated home on every platform

West Babylon
The price is AU$345
includes taxes & fees
7 Dec - 8 Dec
Choice home welcome to the highest rated home on every platform
Marina
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Cove - East Side - Shippan
10.0 out of 10, Exceptional, (23)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
The price is AU$1,121
includes taxes & fees
11 Dec - 12 Dec
Stylish Beach Home near Stamford Downtown/Beach
Fridge, microwave, oven, stovetop
Modern 1 bedroom apartment near Stony Brook university hospital walking distance

Modern 1 bedroom apartment near Stony Brook university hospital walking distance

Stony Brook
10.0 out of 10, Exceptional, (1)
"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 AU$853
includes taxes & fees
8 Dec - 9 Dec
Modern 1 bedroom apartment near Stony Brook university hospital walking distance
Fridge, microwave, oven, stovetop
Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons

Shirley
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is AU$964
includes taxes & fees
3 Dec - 4 Dec
Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop
Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema

Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema

Hicksville
10.0 out of 10, Exceptional, (1)
"Wonderful house for our family trip to Long Island, the perfect space for us and plenty of room for my littles to play. Rooms were spacious and comfortable and the house was clean! "
United States
Abigail F.
The price is AU$659
includes taxes & fees
8 Dec - 9 Dec
Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema
Property grounds
Charming 3-bedroom modern family retreat!

Charming 3-bedroom modern family retreat!

Huntington
9.6 out of 10, Exceptional, (8)
"Great location & thoughtful amenities."
United States
Joshua
The price is AU$735
includes taxes & fees
3 Dec - 4 Dec
Charming 3-bedroom modern family retreat!
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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Top Smithtown Hotel Reviews

Hyatt Regency Long Island

Hyatt Regency Long Island

10/10 Excellent
"The room was perfect. Staff were beyond wonderful, especially Elizabeth at the front desk"
Joseph 1-night trip
Posted 1 day ago
Hyatt Regency Long Island

Find out more about Smithtown

Smithtown Holiday Homes information

Number of reviews
232
Accommodation
544 Holiday Homes
Lowest Price
AU$255
Highest Price
AU$4,135

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