Beautiful golden hour sunrise on the beach at Kings Park Bluffs and Sunken Meadow State Park in Smithtown, NY at dawn. Hot, summer day. Clear, no clouds. Blue sky, coastline of Long Island Sound.

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
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Smithtown holiday homes

Terrace/patio

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$417
includes taxes & fees
15 June - 16 June
Spacious 3BR Family Home Near Everything
Outdoor dining

Cozy 1BR Artist Den Near Oheka Castle & Huntington Village

Cozy 1BR Artist Den Near Oheka Castle & Huntington Village
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is NZ$382
includes taxes & fees
8 July - 9 July
Cozy 1BR Artist Den Near Oheka Castle & Huntington Village
Shower, hair dryer, towels, soap

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
9.4 out of 10, Exceptional, (44 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is NZ$300
includes taxes & fees
16 June - 17 June
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Smart TV, table football, books, stereo

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, (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 NZ$913
includes taxes & fees
15 June - 16 June
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Fridge, microwave, coffee/tea maker, electric kettle

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is NZ$583
includes taxes & fees
27 June - 28 June
Sundown Escape Near SouthShore University Hospital
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 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is NZ$676
includes taxes & fees
15 June - 16 June
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Smart TV

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

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
10.0 out of 10, Exceptional, (4 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is NZ$885
includes taxes & fees
15 June - 16 June
Peaceful private 2-bedroom house in Bayport. Amazing location!
Dining

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, (22 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is NZ$1,614
includes taxes & fees
8 July - 9 July
3 Story Beach Waterview, 3 KING bed, golf putting green!
Shower, hair dryer, soap, toilet paper

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$626
includes taxes & fees
16 June - 17 June
The Royal Suite - Ronkonkoma
TV

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
Rocky Point
7.4 out of 10, Good, (3 reviews)
"The house had everything we needed. I was laid out very well. It was comfortable. The outdoor space was nice."
United States
Carol
The price is NZ$1,048
includes taxes & fees
15 June - 16 June
Charming Rocky Point Home ~ 1 Mi to Beach!
Fridge, microwave, oven, stovetop

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Fairfield Beach
10.0 out of 10, Exceptional, (24 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
The price is NZ$1,475
includes taxes & fees
17 June - 18 June
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Marina

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, (79 reviews)
"A true port in the storm"
United States
Trey S.
The price is NZ$1,081
includes taxes & fees
16 June - 17 June
Captain's Cottage - Cold Spring Harbor Water Views
Fridge, microwave, oven, stovetop

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very good, (10 reviews)
"Great stay! "
United States
Emily S.
The price is NZ$1,021
includes taxes & fees
16 June - 17 June
Tranquil Stay
Property grounds

Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
10.0 out of 10, Exceptional, (1 review)
"The host was very helpful and amazing. He also assisted us with transportation due to a mishap with our car rental. However if you want a peaceful and relaxing trip in Long Island please book this place. Reggie is an amazing guy .Thank you for hosting us"
United States
Lakisha M.
The price is NZ$676
includes taxes & fees
25 June - 26 June
Bright & Comfortable Home in the Heart of It All
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, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is NZ$1,176
includes taxes & fees
28 June - 29 June
Modern Vacation home. Close to The Hamptons
Outdoor spa tub

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is NZ$1,622
includes taxes & fees
22 June - 23 June
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Property grounds

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is NZ$2,343
includes taxes & fees
15 June - 16 June
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Interior

Stay at Black Rock Harbor

Stay at Black Rock Harbor
Black Rock Historic District
10.0 out of 10, Exceptional, (26 reviews)
"This house was perfect for our family. Will definitely use again when we're visiting family in the area."
United States
Laura L.
The price is NZ$1,938
includes taxes & fees
1 July - 2 July
Stay at Black Rock Harbor
Exterior

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife
Northport
9.4 out of 10, Exceptional, (17 reviews)
"Great host and property!"
United States
Anonymous traveller
The price is NZ$2,128
includes taxes & fees
22 June - 23 June
World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is NZ$1,643
includes taxes & fees
19 June - 20 June
Waterview House Walking Distance from Cove Beach
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

Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

6/10 Okay
"The check-in was very slow. When I arrived, there were two people doing that job. Then one left after he finished with the people he was helping. This left just one person who had some difficulties with the couple he was checking in. I waited approximately 10-15 minutes to check in and there was a couple behind me who waited even longer. My WiFi didn't work. Fortunately, the two young men at the desk were able to do something involving a hot spot and got it to function. There was a false fire alarm, which required that I walk down 5 flights of steps to avoid the elevator. I was not aware of when the all clear sounded and had to ask someone if it was ok to go back to the room, and it was. The toilet did not flush properly. I called the desk and asked for assistance. They said that they would send somebody right up. Forty-five minutes later, when nobody had shown up, I called again. This time a man came about fifteen minutes later. He didn't really fix the flush but showed me how to get around it by holding the flusher knob for several seconds until I saw the water swirling and going down the toilet. I had the do-not-disturb tag hanging on the outside of the door, but the cleaning lady entered the room anyway."
David 2-night trip
Posted 4 hours ago
Radisson Hotel Hauppauge-Long Island

Find out more about Smithtown

Smithtown Holiday Homes information

Number of reviews
216
Accommodation
486 Holiday Homes
Lowest Price
NZ$300
Highest Price
NZ$2,343