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

Smithtown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Smithtown vacation rentals

A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

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, (53 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
$144 nightly
The price is $165
Oct 3 - Oct 4
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

2. 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, (30 reviews)
"The property was very easy to find, clean, and comfortable. The hosts were very communicative and accommodating. Highly recommend!"
United States
Karen D.
$157 nightly
The price is $179
Oct 5 - Oct 6
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

3. 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.
$301 nightly
The price is $344
Oct 5 - Oct 6
Total with taxes and fees
The Royal Suite - Ronkonkoma
A compact kitchen with white cabinets, a black stove, and a stainless steel sink.

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

Cozy 1-bedroom apartment in charming Centereach with AC
Centereach
$183 nightly
The price is $209
Oct 25 - Oct 26
Total with taxes and fees
Cozy 1-bedroom apartment in charming Centereach with AC
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

5. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
$278 nightly
The price is $318
Oct 5 - Oct 6
Total with taxes and fees
Spacious 3BR Family Home Near Everything
A modern bedroom with a large bed, a bedside table, a sofa, and a potted plant.

6. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Exactly as advertised, comfortable bed easy entry, overall great experience."
United States
Monte P.
$154 nightly
The price is $176
Oct 4 - Oct 5
Total with taxes and fees
1 bedroom 1 bath private entrance
A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

7. 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
$222 nightly
The price is $254
Oct 4 - Oct 5
Total with taxes and fees
Private 1 bedroom apt in a quiet neighborhood, close to all!
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.

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.
$301 nightly
The price is $343
Oct 5 - Oct 6
Total with taxes and fees
Spacious one Bedroom Apt with private entrance
A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

9. 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
$265 nightly
The price is $303
Oct 8 - Oct 9
Total with taxes and fees
Sundown Escape-South Shore Long Island
Interior

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
$427 nightly
The price is $488
Oct 22 - Oct 23
Total with taxes and fees
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A modern kitchen with wooden cabinets and a granite countertop.

11. 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
$191 nightly
The price is $218
Oct 13 - Oct 14
Total with taxes and fees
Your Perfect Getaway Between Farmingdale & Amityville
A living room with a blue door, a white shelf, a grey sofa with patterned cushions, and a small table with a decorative item.

12. 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.
$448 nightly
The price is $511
Oct 5 - Oct 6
Total with taxes and fees
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.

13. 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
$235 nightly
The price is $270
Oct 7 - Oct 8
Total with taxes and fees
DUNE Fairfield Beach
A modern kitchen with a stainless steel sink, a white countertop, and a backsplash with a mosaic tile pattern.

14. Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
$313 nightly
The price is $343
Oct 4 - Oct 5
Total with taxes and fees
Sundown Escape Near SouthShore University Hospital
Exterior

15. 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.
$275 nightly
The price is $314
Oct 5 - Oct 6
Total with taxes and fees
Welcoming 1 bedroom apartment in beautiful harbor village.
A kitchen with white cabinets, a microwave, a stove, and a sink. There is a window with blinds, a trash can, and a wooden stool.

16. Charming Secluded Waterfront retreat

Charming Secluded Waterfront retreat
Oakdale
$241 nightly
The price is $275
Oct 8 - Oct 9
Total with taxes and fees
Charming Secluded Waterfront retreat
A room with a closed door, a potted plant, a small table with a sign, and a wall with a decorative sign.

17. 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.
$235 nightly
The price is $268
Oct 4 - Oct 5
Total with taxes and fees
Cozy king suite with kitchen and dining area.
An outdoor patio area with a grill, seating, and string lights.

18. 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.
$307 nightly
The price is $351
Oct 20 - Oct 21
Total with taxes and fees
Private Apartment on River Ave. close to main st
A water park with multiple slides and pools, surrounded by trees and a parking lot.

19. 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.
$398 nightly
The price is $418
Oct 5 - Oct 6
Total with taxes and fees
Private 3Br Apt: King-2Queen -PetPally -LTR-STR
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
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.
$309 nightly
The price is $353
Oct 5 - Oct 6
Total with taxes and fees
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
"The room was clean and very comfortable. The staff was very welcoming and considerate!"
April 1-night trip
Posted 9 hours ago
The Circle Hotel Fairfield

Find out more about Smithtown

Everything you need to know about Smithtown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smithtown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Smithtown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $165 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smithtown rentals

At Expedia, we put the best Smithtown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Large Beach House Steps From Town and Ocean: This vacation 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 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.