Smithtown Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Smithtown holiday rentals

A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

1. Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (35 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is AU$245
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

2. 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$246
includes taxes & fees
6 Nov - 7 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

3. Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (30 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is AU$347
includes taxes & fees
10 Nov - 11 Nov
Private 1 bedroom apt in a quiet neighborhood, close to all!
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

4. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$454
includes taxes & fees
9 Nov - 10 Nov
Spacious 3BR Family Home Near Everything
A wooden outdoor seating area with a bench and two chairs, a brick wall, and a window.

5. Central 2BR, Garden Suite, Top Amenities & Care!

Central 2BR, Garden Suite, Top Amenities & Care!
Central Islip
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, clean and inviting space. Thanks for a great space away from home; will definietly book again."
United States
Vladamir R.
The price is AU$767
includes taxes & fees
12 Nov - 13 Nov
Central 2BR, Garden Suite, Top Amenities & Care!
A bedroom with a bed, a bedside lamp, a TV, and a door leading to another room.

6. Cozy 1-bedroom apartment in charming Centereach with AC

Cozy 1-bedroom apartment in charming Centereach with AC
Centereach
The price is AU$242
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-bedroom apartment in charming Centereach with AC
A wooden deck with a white railing, a set of stairs, and outdoor furniture.

7. 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$650
includes taxes & fees
23 Nov - 24 Nov
Bright & Comfortable Home in the Heart of It All
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

8. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (118 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is AU$369
includes taxes & fees
6 Dec - 7 Dec
DUNE Fairfield Beach
A modern living room with a grey sectional sofa, a round coffee table, and a dining area with a small table and chairs.

9. Cozy 1-bedroom apartment in lovely Central Islip

Cozy 1-bedroom apartment in lovely Central Islip
Central Islip
The price is AU$249
includes taxes & fees
4 Dec - 5 Dec
Cozy 1-bedroom apartment in lovely Central Islip
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

10. 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$497
includes taxes & fees
25 Nov - 26 Nov
The Royal Suite - Ronkonkoma
A living room with a brown sofa, a glass coffee table with decorative items, and a kitchen in the background with wooden cabinets and a black refrigerator.

11. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.2 out of 10, Very good, (12 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is AU$458
includes taxes & fees
9 Nov - 10 Nov
Spacious one Bedroom Apt with private entrance
Property grounds

12. Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong

Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong
Dix Hills
The price is AU$332
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong
A modern bedroom with a large bed, a bedside table, a sofa, and a potted plant.

13. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.4 out of 10, Very good, (28 reviews)
"Exactly as advertised, comfortable bed easy entry, overall great experience."
United States
Monte P.
The price is AU$271
includes taxes & fees
15 Nov - 16 Nov
1 bedroom 1 bath private entrance
A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

14. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is AU$428
includes taxes & fees
19 Nov - 20 Nov
Sundown Escape-South Shore Long Island
A modern kitchen with a stainless steel sink, a white countertop, and a backsplash with a mosaic tile pattern.

15. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is AU$454
includes taxes & fees
19 Nov - 20 Nov
Sundown Escape Near SouthShore University Hospital
Kitchen | Electric Kettle | Toaster | Blender

16. Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Deer Park
9.0 out of 10, Wonderful, (4 reviews)
"My family and I really enjoyed this property! The host was welcoming, the property was clean and well-cared for, and it’s in a very nice area. We would stay again next time we’re in Long Island!"
United States
Danielle M.
The price is AU$656
includes taxes & fees
15 Nov - 16 Nov
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A dining area with a table, chairs, a vase with flowers, and a sign that reads 'Relax Unwind & Enjoy'.

17. Charming Secluded Waterfront retreat

Charming Secluded Waterfront retreat
Oakdale
10.0 out of 10, Exceptional, (1 review)
"If we could give 10 stars, we would. Every detail was very thoughtfully planned. Comfortable bed, quiet and peaceful location. Great communication. We will stay again."
United States
Loritha F.
The price is AU$375
includes taxes & fees
17 Nov - 18 Nov
Charming Secluded Waterfront retreat
Exterior

18. Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean upstairs apartment with a private entrance. Very quiet neighborhood with a small park across the street. Karen, the homeowner who lives downstairs is a wonderful person. The place was perfect for what I needed amd the location was great."
United States
Sallyann S.
The price is AU$420
includes taxes & fees
8 Nov - 9 Nov
Welcoming 1 bedroom apartment in beautiful harbor village.
A modern kitchen with dark cabinetry, a microwave, and a stove. There is a large flat-screen TV mounted on the wall.

19. SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (10 reviews)
"Great location and cozy studio."
United States
Joseph F.
The price is AU$530
includes taxes & fees
9 Nov - 10 Nov
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
A living room with a large mirror, a grey sofa, a small round table with a plant, and a grey throw blanket.

20. 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$469
includes taxes & fees
10 Nov - 11 Nov
Modern 2BR Retreat w/ Full Kitchen & Living
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

A hotel with a parking lot, a large building with multiple floors, and a forested area in the background.
Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook
Stony Brook

10/10 Excellent

We’ve stayed here twice now and dined in multiple times. It’s a lovely warm and inviting place to stay. Staff are excellent are the amenities. Highly recommended.
Australia
Carl
Reviewed July 27, 2026
Hilton Garden Inn Stony Brook

Find out more about Smithtown

Everything you need to know about Smithtown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smithtown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Smithtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smithtown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smithtown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smithtown holiday rentals we have selected for you start as low as AU$241 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Smithtown rentals

At Expedia, we put the best Smithtown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Smithtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smithtown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smithtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there holiday rentals in Smithtown?

Yes, there are holiday rentals in Smithtown close to Blydenburgh County Park, or you can select a more secluded option if you're looking for a relaxing stay. Smithtown is known for its lake views.

What are some of the best holiday rentals that Smithtown has to offer?

Large Beach House Steps From Town and Ocean: This holiday home rental outside of Smithtown has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Smithtown?

Family-friendly attractions include Blydenburgh County Park, whereas Nissequogue River is a spot to enjoy the outdoors. Stonebridge Golf Links and Country Club and paces steakhouse are other places to visit while you're in town.

What are holiday rentals like in Smithtown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smithtown. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for small groups.