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

Smithtown Holiday Rentals

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Our top choices for Smithtown holiday rentals

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
9.8 out of 10, Exceptional, (29 reviews)
"The property was very easy to find, clean, and comfortable. The hosts were very communicative and accommodating. Highly recommend!"
United States
Karen D.
The price is NZ$339
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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, (52 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$287
includes taxes & fees
28 Sept - 29 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

3. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$555
includes taxes & fees
6 Oct - 7 Oct
Spacious 3BR Family Home Near Everything

4. 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 NZ$523
includes taxes & fees
28 Sept - 29 Sept
Sundown Escape-South Shore Long Island

5. 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, (29 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 NZ$499
includes taxes & fees
28 Sept - 29 Sept
Private 1 bedroom apt in a quiet neighborhood, close to all!

6. 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 NZ$869
includes taxes & fees
29 Sept - 30 Sept
Bright & Comfortable Home in the Heart of It All

7. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (9 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$587
includes taxes & fees
5 Oct - 6 Oct
The Royal Suite - Ronkonkoma

8. 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 NZ$542
includes taxes & fees
27 Sept - 28 Sept
Welcoming 1 bedroom apartment in beautiful harbor village.

9. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is NZ$463
includes taxes & fees
28 Sept - 29 Sept
DUNE Fairfield Beach

10. Private 3Br Apt: King-2Queen -PetPally -LTR-STR

Private 3Br Apt: King-2Queen -PetPally -LTR-STR
Bay Shore
10.0 out of 10, Exceptional, (1 review)
The price is NZ$721
includes taxes & fees
2 Oct - 3 Oct
Private 3Br Apt: King-2Queen -PetPally -LTR-STR

11. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.0 out of 10, Very good, (11 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 NZ$608
includes taxes & fees
11 Oct - 12 Oct
Spacious one Bedroom Apt with private entrance

12. 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)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is NZ$724
includes taxes & fees
15 Oct - 16 Oct
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

13. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is NZ$584
includes taxes & fees
28 Sept - 29 Sept
Sundown Escape Near SouthShore University Hospital

14. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is NZ$467
includes taxes & fees
27 Sept - 28 Sept
Cozy king suite with kitchen and dining area.

15. Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (5 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is NZ$734
includes taxes & fees
28 Sept - 29 Sept
Luxe Provincial Style Studio w/ Patio & Parking

16. 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 NZ$2,256
includes taxes & fees
1 Oct - 2 Oct
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

17. 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, (85 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is NZ$913
includes taxes & fees
28 Sept - 29 Sept
Captain's Cottage - Cold Spring Harbor Water Views

18. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (16 reviews)
"Love being able to park off the street."
United States
Joan
The price is NZ$377
includes taxes & fees
28 Sept - 29 Sept
Your Perfect Getaway Between Farmingdale & Amityville

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

Modern 2BR Retreat w/ Full Kitchen & Living
Deer Park
6.0 out of 10, (2 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 NZ$602
includes taxes & fees
28 Sept - 29 Sept
Modern 2BR Retreat w/ Full Kitchen & Living

20. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Clean and friendly owners it’s in the side of there home but very peaceful no complaints "
United States
Matthew B.
The price is NZ$307
includes taxes & fees
4 Oct - 5 Oct
1 bedroom 1 bath private entrance
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Smithtown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Smithtown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Smithtown. Seeing all the best attractions is bound to make you fall in love with Smithtown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Smithtown short-term rentals, that won’t be hard to do.

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?

Nissequogue River and Caleb Smith State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Blydenburgh County Park. 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.