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

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, (48 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 NZ$311
includes taxes & fees
6 Aug - 7 Aug
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (8 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$603
includes taxes & fees
26 Aug - 27 Aug
The Royal Suite - Ronkonkoma

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$597
includes taxes & fees
2 Aug - 3 Aug
Spacious 3BR Family Home Near Everything

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, (2 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 NZ$882
includes taxes & fees
23 Aug - 24 Aug
Bright & Comfortable Home in the Heart of It All

Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!
Lake Grove
8.0 out of 10, Very good, (42 reviews)
"Plenty of room, comfortable, great outdoor space, conveniently located to grocery stores and restaurants, great communication from owner."
United States
Raymond
The price is NZ$1,295
includes taxes & fees
31 July - 1 Aug
Spacious Home Located Close to Stony Brook!

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is NZ$583
includes taxes & fees
6 Aug - 7 Aug
Sundown Escape Near SouthShore University Hospital

Waterfront Paradise Private Beach + Dock + Hot tub

Waterfront Paradise Private Beach + Dock + Hot tub
Saint James
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 NZ$3,104
includes taxes & fees
30 July - 31 July
Waterfront Paradise Private Beach + Dock + Hot tub

3-bedroom cozy home in wonderful Selden , Great location close to all.

3-bedroom cozy home in wonderful Selden , Great location close to all.
Selden
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home. Very comfortable. Didn’t get to enjoy the outside but would definitely come again "
United States
Fran H.
The price is NZ$1,526
includes taxes & fees
9 Aug - 10 Aug
3-bedroom cozy home in wonderful Selden , Great location close to all.

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$725
includes taxes & fees
19 Aug - 20 Aug
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
9.4 out of 10, Exceptional, (6 reviews)
"Quiet and respectful owner. Welcoming and a great nights sleep. "
United States
Jason P.
The price is NZ$875
includes taxes & fees
9 Aug - 10 Aug
Peaceful private 2-bedroom house in Bayport. Amazing location!

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$923
includes taxes & fees
3 Aug - 4 Aug
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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, (82 reviews)
"Perfect spot. Gorgeous view. "
United States
Trina A.
The price is NZ$1,071
includes taxes & fees
30 July - 31 July
Captain's Cottage - Cold Spring Harbor Water Views

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 NZ$1,391
includes taxes & fees
4 Aug - 5 Aug
3 Story Beach Waterview, 3 KING bed, golf putting green!

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 location & thoughtful amenities."
United States
Joshua
The price is NZ$1,045
includes taxes & fees
9 Aug - 10 Aug
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

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, (12 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is NZ$2,318
includes taxes & fees
23 Aug - 24 Aug
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

Tranquil Stay

Tranquil Stay
Shirley
8.2 out of 10, Very good, (11 reviews)
"Great stay! "
United States
Emily S.
The price is NZ$1,244
includes taxes & fees
2 Aug - 3 Aug
Tranquil Stay

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$1,404
includes taxes & fees
3 Aug - 4 Aug
Modern Vacation home. Close to The Hamptons

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is NZ$1,499
includes taxes & fees
4 Aug - 5 Aug
Stylish Beach Home near Stamford Downtown/Beach

5 minute walk to beach, walk to town & train

5 minute walk to beach, walk to town & train
Fairfield Beach
10.0 out of 10, Exceptional, (26 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
5 minute walk to beach, walk to town & train

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is NZ$1,291
includes taxes & fees
4 Aug - 5 Aug
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
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
218
Accommodation
426 Holiday Homes
Lowest Price
NZ$311
Highest Price
NZ$3,104