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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)
The price is €155
includes taxes & fees
14 Nov - 15 Nov

2. Spacious 3BR Family Home Near Everything
Spacious 3BR Family Home Near EverythingCentral Islip
The price is €283
includes taxes & fees
18 Nov - 19 Nov

3. The Royal Suite - Ronkonkoma
The Royal Suite - RonkonkomaRonkonkoma
9.8 out of 10, Exceptional, (10 reviews)
The price is €316
includes taxes & fees
25 Nov - 26 Nov

4. Bright & Comfortable Home in the Heart of It All
Bright & Comfortable Home in the Heart of It AllCentral Islip
8.8 out of 10, Excellent, (3 reviews)
The price is €412
includes taxes & fees
23 Nov - 24 Nov

5. Sundown Escape Near SouthShore University Hospital
Sundown Escape Near SouthShore University HospitalBay Shore
The price is €291
includes taxes & fees
20 Nov - 21 Nov

6. Modern 2BR Retreat w/ Full Kitchen & Living
Modern 2BR Retreat w/ Full Kitchen & LivingDeer Park
7.4 out of 10, Good, (3 reviews)
The price is €299
includes taxes & fees
9 Nov - 10 Nov

7. Peaceful 3BR Garden Cottage Long Island Escape
Peaceful 3BR Garden Cottage Long Island EscapeCoram
10.0 out of 10, Exceptional, (1 review)
The price is €407
includes taxes & fees
8 Nov - 9 Nov

8. Historic Home near Stony Brook Village & Beach
Historic Home near Stony Brook Village & BeachStony Brook
7.4 out of 10, Good, (3 reviews)
The price is €725
includes taxes & fees
9 Nov - 10 Nov

9. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Ultra-Modern Studio | Near Hospital & NYCIM | WiFiHuntington
10.0 out of 10, Exceptional, (5 reviews)
The price is €348
includes taxes & fees
8 Nov - 9 Nov

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 WingCommack
10.0 out of 10, Exceptional, (14 reviews)
The price is €1,117
includes taxes & fees
9 Nov - 10 Nov

11. Captain's Cottage - Cold Spring Harbor Water Views
Captain's Cottage - Cold Spring Harbor Water ViewsCold Spring Harbor
10.0 out of 10, Exceptional, (89 reviews)
The price is €474
includes taxes & fees
16 Nov - 17 Nov

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)
The price is €251
includes taxes & fees
9 Nov - 10 Nov

13. Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extras
Spacious 4BR house Ronkonkoma, NY. Central AC, WiFi...heated pool, many extrasRonkonkoma
3.0 out of 10, (2 reviews)
The price is €750
includes taxes & fees
14 Nov - 15 Nov

14. Huntington Village 4BR Walkable Sleeps 8
Huntington Village 4BR Walkable Sleeps 8Huntington
10.0 out of 10, Exceptional, (5 reviews)
The price is €718
includes taxes & fees
9 Nov - 10 Nov

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)
The price is €593
includes taxes & fees
17 Nov - 18 Nov

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 NYRocky Point
10.0 out of 10, Exceptional, (29 reviews)
The price is €485
includes taxes & fees
20 Nov - 21 Nov

17. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington VillageHuntington
9.2 out of 10, Wonderful, (12 reviews)
The price is €544
includes taxes & fees
16 Nov - 17 Nov

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 beachFire Island
9.8 out of 10, Exceptional, (7 reviews)
The price is €1,068
includes taxes & fees
8 Nov - 9 Nov

19. Modern Vacation home. Close to The Hamptons
Modern Vacation home. Close to The HamptonsShirley
9.8 out of 10, Exceptional, (7 reviews)
The price is €468
includes taxes & fees
8 Nov - 9 Nov

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 NYCMassapequa
10.0 out of 10, Exceptional, (12 reviews)
The price is €2,605
includes taxes & fees
8 Nov - 9 Nov
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.
Learn more about Smithtown
Stroll through the charming Caleb Smith State Park Preserve, where hiking trails wind through lush forests and past tranquil ponds. History buffs can explore the Smithtown Historical Society's buildings, then grab a bite at one of the cosy Main Street eateries.

Top reviews in Smithtown

Homewood Suites by Hilton Ronkonkoma
Homewood Suites by Hilton RonkonkomaRonkonkoma











































































