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

Smithtown Vacation Rentals

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Our top choices for Smithtown vacation 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
10.0 out of 10, Exceptional, (26 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is CA $168
CA $247 total
includes taxes & fees
Aug 31 - Sep 1
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, (49 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 CA $137
CA $228 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $265
CA $440 total
includes taxes & fees
Aug 28 - Aug 29
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 CA $166
CA $395 total
includes taxes & fees
Sep 14 - Sep 15
Sundown Escape-South Shore Long Island

5. 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 CA $222
CA $660 total
includes taxes & fees
Sep 9 - Sep 10
Bright & Comfortable Home in the Heart of It All

6. 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 CA $244
CA $587 total
includes taxes & fees
Sep 1 - Sep 2
The Royal Suite - Ronkonkoma

7. Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
8.0 out of 10, Very good, (9 reviews)
"Great host, nice place."
United States
Brian C.
The price is CA $167
CA $303 total
includes taxes & fees
Sep 21 - Sep 22
Tiny Home Private, Students, Nurses, Tech

8. 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 CA $156
CA $472 total
includes taxes & fees
Sep 1 - Sep 2
Spacious one Bedroom Apt with private entrance

9. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is CA $156
CA $265 total
includes taxes & fees
Sep 8 - Sep 9
1 bedroom 1 bath private entrance

10. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is CA $199
CA $472 total
includes taxes & fees
Sep 14 - Sep 15
Sundown Escape Near SouthShore University Hospital

11. 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 CA $331
CA $521 total
includes taxes & fees
Sep 1 - Sep 2
Private 1 bedroom apt in a quiet neighborhood, close to all!

12. 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 CA $263
CA $430 total
includes taxes & fees
Sep 1 - Sep 2
Welcoming 1 bedroom apartment in beautiful harbor village.

13. 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)
"These were nice rooms. Very professionally set-up."
United States
Marcus P.
The price is CA $327
CA $555 total
includes taxes & fees
Sep 8 - Sep 9
Private 3Br Apt: King-2Queen -PetPally -LTR-STR

14. Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is CA $242
CA $368 total
includes taxes & fees
Sep 1 - Sep 2
Cozy king suite with kitchen and dining area.

15. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (111 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $244
CA $365 total
includes taxes & fees
Sep 13 - Sep 14
DUNE Fairfield Beach

16. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (13 reviews)
"Love being able to park off the street."
United States
Joan
The price is CA $147
CA $296 total
includes taxes & fees
Aug 31 - Sep 1
Your Perfect Getaway Between Farmingdale & Amityville

17. 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 CA $325
CA $602 total
includes taxes & fees
Aug 31 - Sep 1
Luxe Provincial Style Studio w/ Patio & Parking

18. 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, (9 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is CA $309
CA $582 total
includes taxes & fees
Aug 31 - Sep 1
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

19. East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (19 reviews)
"Everything was good"
United States
Elena
The price is CA $164
CA $275 total
includes taxes & fees
Aug 27 - Aug 28
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

20. Private Apartment on River Ave. close to main st

Private Apartment on River Ave. close to main st
Patchogue
9.6 out of 10, Exceptional, (8 reviews)
"Nice little property. Perfect for what we needed. Host was great."
United States
A H.
The price is CA $340
CA $622 total
includes taxes & fees
Sep 2 - Sep 3
Private Apartment on River Ave. close to main st
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Smithtown?

Yes, there are vacation rentals in Smithtown close to Blydenburgh County Park, or you can choose a more remote option if you're looking for extra privacy while you relax. Smithtown is known for its lake views.

What are some of the best vacation home rentals in Smithtown?

Charming Home in Seaside: This vacation home rental outside of Smithtown is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 vacation rentals like in Smithtown?

Vacation rentals are private properties you can book for a couple days or more in Smithtown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.