A rocky beach with large boulders and a clear view of the ocean.

Holiday Homes in Smithtown

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Our top choices for Smithtown holiday homes

1. 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, (57 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is AU$248
includes taxes & fees
13 Nov - 14 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

2. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$459
includes taxes & fees
19 Nov - 20 Nov
Spacious 3BR Family Home Near Everything

3. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (10 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$500
includes taxes & fees
25 Nov - 26 Nov
The Royal Suite - Ronkonkoma

4. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is AU$663
includes taxes & fees
23 Nov - 24 Nov
Bright & Comfortable Home in the Heart of It All

5. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is AU$459
includes taxes & fees
20 Nov - 21 Nov
Sundown Escape Near SouthShore University Hospital

6. Modern 2BR Retreat w/ Full Kitchen & Living

Modern 2BR Retreat w/ Full Kitchen & Living
Deer Park
7.4 out of 10, Good, (3 reviews)
"Needs lots of repairs and cleaning.Didn’t understand how one room had two AC and two TV while the other room had none. I would liked to hang out on the porch but also not clean and there was no table but a couple dirty chairs."
United States
marlene D.
The price is AU$474
includes taxes & fees
15 Nov - 16 Nov
Modern 2BR Retreat w/ Full Kitchen & Living

7. Peaceful 3BR Garden Cottage Long Island Escape

Peaceful 3BR Garden Cottage Long Island Escape
Coram
10.0 out of 10, Exceptional, (1 review)
"Excellent host and peaceful getaway. I highly recommend!"
United States
Greg M.
The price is AU$669
includes taxes & fees
10 Nov - 11 Nov
Peaceful 3BR Garden Cottage Long Island Escape

8. Historic Home near Stony Brook Village & Beach

Historic Home near Stony Brook Village & Beach
Stony Brook
7.4 out of 10, Good, (3 reviews)
"V1 church was nearby "
United States
david w.
The price is AU$1,140
includes taxes & fees
8 Nov - 9 Nov
Historic Home near Stony Brook Village & Beach

9. 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 AU$562
includes taxes & fees
8 Nov - 9 Nov
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10. 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, (14 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is AU$1,710
includes taxes & fees
8 Nov - 9 Nov
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

11. 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, (89 reviews)
"Comfortable beds and close to good food"
United States
Stacey S.
The price is AU$731
includes taxes & fees
16 Nov - 17 Nov
Captain's Cottage - Cold Spring Harbor Water Views

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

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
8.8 out of 10, Excellent, (8 reviews)
"He’s an excellent hosts and his place is well worth it."
United States
Rowena V.
The price is AU$403
includes taxes & fees
15 Nov - 16 Nov
Peaceful private 2-bedroom house in Bayport. Amazing location!

13. Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras
Ronkonkoma
3.0 out of 10, (2 reviews)
"My sister got to the property before me and there were extra guests the owner of the property got in contact with me to let me know what was happening and told me to get everyone out or my stay would be terminated I got to the house and mad everyone leave . There was only 2 people in the house and my 2 year old son and he asked us to leave after he told me if I got everyone out I could stay. It was 1 am and I did everything he asked me to do. "
United States
Mitania L.
The price is AU$1,148
includes taxes & fees
11 Nov - 12 Nov
Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras

14. Huntington Village 4BR Walkable Sleeps 8

Huntington Village 4BR Walkable Sleeps 8
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"The house was in an ideal location! Unfortunately, there was a nor easterner so walking was not an option but on a lovely day, it would be a perfect house to stay in and explore Huntington! The bedrooms were ideal."
United States
Susan
The price is AU$1,122
includes taxes & fees
10 Nov - 11 Nov
Huntington Village 4BR Walkable Sleeps 8

15. 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, (24 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AU$960
includes taxes & fees
17 Nov - 18 Nov
3 Story Beach Waterview, 3 KING bed, golf putting green!

16. 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, (29 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 AU$758
includes taxes & fees
16 Nov - 17 Nov
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

17. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Huntington
9.2 out of 10, Wonderful, (12 reviews)
"Great place to stay"
United States
Michael D.
The price is AU$850
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

18. Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.8 out of 10, Exceptional, (7 reviews)
"Great location to the beach, owner was extremely nice. My family had a great time."
United States
Gregory C.
The price is AU$1,704
includes taxes & fees
18 Nov - 19 Nov
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

19. Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
9.8 out of 10, Exceptional, (7 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is AU$749
includes taxes & fees
8 Nov - 9 Nov
Modern Vacation home. Close to The Hamptons

20. 4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC

4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC
Massapequa
10.0 out of 10, Exceptional, (12 reviews)
"Just a comfortable, pleasant experience for four generations of family, ages 1 month to 80 Room to spread out, house functions so well. Lots of amenities Restaurants nearby"
United States
Madeleine T.
The price is AU$4,113
includes taxes & fees
15 Nov - 16 Nov
4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC
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

Find out more about Smithtown

Smithtown Holiday Homes information

Number of reviews
283
Accommodation
349 Holiday Homes
Lowest Price
AU$248
Highest Price
AU$4,113

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