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Smithtown Holiday Rentals

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Our top choices for Smithtown holiday rentals

JC Entire Apartment remodeled, close to Airport and Ferry

JC Entire Apartment remodeled, close to Airport and Ferry
Coram
10.0 out of 10, Exceptional, (3)
"Would definitely stay again "
United States
Katherine R.
The price is AU$307
includes taxes & fees
7 Jan - 8 Jan 2026
JC Entire Apartment remodeled, close to Airport and Ferry

Cozy 2 bedroom retreat in long island

Cozy 2 bedroom retreat in long island
2.0 star property
Central Islip
8.8 out of 10, Excellent, (3)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is AU$381
includes taxes & fees
18 Dec - 19 Dec
Cozy 2 bedroom retreat in long island

South Shore Studio in Mastic

South Shore Studio in Mastic
2.0 star property
Mastic
10.0 out of 10, Exceptional, (2)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is AU$292
includes taxes & fees
17 Dec - 18 Dec
South Shore Studio in Mastic

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Cozy Country Cottage #4

Cozy Country Cottage #4
Miller Place
10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is AU$495
includes taxes & fees
17 Dec - 18 Dec
Cozy Country Cottage #4

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
8.4 out of 10, Very good, (6)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
The price is AU$301
includes taxes & fees
18 Dec - 19 Dec
Tiny Home Private, Students, Nurses, Tech

Zen Oasis - Pvt. Entry Studio Bed+Bath by NUMC

Zen Oasis - Pvt. Entry Studio Bed+Bath by NUMC
East Meadow
10.0 out of 10, Exceptional, (11)
"Very easy check in process, great communication with host, close to so many venues and the beach is just a short drive away!!"
United States
Joanne P.
The price is AU$243
includes taxes & fees
17 Dec - 18 Dec
Zen Oasis - Pvt. Entry Studio Bed+Bath by NUMC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.2 out of 10, Wonderful, (9)
"Had a great stay "
United States
Desiree
The price is AU$246
includes taxes & fees
17 Dec - 18 Dec
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is AU$520
includes taxes & fees
18 Dec - 19 Dec
Spacious one Bedroom Apt with private entrance

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.4 out of 10, Exceptional, (3)
"Fantastic! Well communicated and perfectly described! Highly recommend and thank you!"
United States
Wayne L.
The price is AU$327
includes taxes & fees
17 Dec - 18 Dec
Your Perfect Getaway Between Farmingdale & Amityville

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, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is AU$250
includes taxes & fees
17 Dec - 18 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
Kings Park
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is AU$272
includes taxes & fees
21 Dec - 22 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Cozy Country Cottage #2

Cozy Country Cottage #2
Miller Place
9.0 out of 10, Wonderful, (15)
"House was well kept, comfortable bed, the location was near shopping & beach. Owner was pleasant and helpful."
United States
Joan S.
The price is AU$514
includes taxes & fees
23 Dec - 24 Dec
Cozy Country Cottage #2

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, (21)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is AU$948
includes taxes & fees
17 Dec - 18 Dec
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy and Modern 2-bedroom apartment in lovely Yaphank

Cozy and Modern 2-bedroom apartment in lovely Yaphank
2.0 star property
Yaphank
The price is AU$567
includes taxes & fees
17 Dec - 18 Dec
Cozy and Modern 2-bedroom apartment in lovely Yaphank

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (26)
"Great location, great host, and nice rental especially for the price! Everything went smoothly and we will be returning next year."
United States
Joshua W.
The price is AU$352
includes taxes & fees
20 Dec - 21 Dec
Walk to Beach 2BR Near Dining & Shopping

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

Peaceful private 2-bedroom house in Bayport.Amazing location!
2.0 star property
Bayport
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is AU$419
includes taxes & fees
17 Dec - 18 Dec
Peaceful private 2-bedroom house in Bayport.Amazing location!

Hottub, ⛳️, htd pool, Sauna, Basketball

Hottub, ⛳️, htd pool, Sauna, Basketball
Mastic
10.0 out of 10, Exceptional, (27)
"Excellent accommodations for a large family gathering.The home is inviting and comfortable. It offers many amenities and the host is very hospitable. "
United States
Maria C.
The price is AU$1,686
includes taxes & fees
17 Dec - 18 Dec
Hottub, ⛳️, htd pool, Sauna, Basketball

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, (26)
"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$390
includes taxes & fees
17 Dec - 18 Dec
Private 1 bedroom apt in a quiet neighborhood, close to all!

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
8.6 out of 10, Excellent, (12)
"I loved staying there very clean and quiet. I will definitely come back. Nice neighborhood "
United States
Ana M.
The price is AU$270
includes taxes & fees
17 Dec - 18 Dec
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
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

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$250 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?

Modern Vacation home. Close to The Hamptons: This holiday home rental outside of Smithtown is located on the waterfront, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 Caleb Smith State Park 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.