Photo by Doug Kerr

Smithtown Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Smithtown holiday rentals

6.8 out of 10, (3)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
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

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.4 out of 10, Very good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$555
includes taxes & fees
20 Dec - 21 Dec
Guesthouse at Norwalk Inn
10.0 out of 10, Exceptional, (14)
"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 NZ$309
includes taxes & fees
26 Dec - 27 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Holiday Home in Stony Brook

Beautiful historic home in Stony Brook!
2.0 star property
8.2 out of 10, Very good, (20)
"Beautiful home in a beautiful location! We enjoyed it so much we extended our stay! "
United States
Antoinette W.
Beautiful historic home in Stony Brook!
10.0 out of 10, Exceptional, (4)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is NZ$1,060
includes taxes & fees
22 Dec - 23 Dec
Modern Vacation home. Close to The Hamptons
10.0 out of 10, Exceptional, (89)
"A special place and love staying here in this lovely home - looking forward to our next stay!"
United States
Roxanne M.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

Cottage in Miller Place

Cozy Country Cottage #3
10.0 out of 10, Exceptional, (32)
"Fantastic stay! "
United States
Michael V.
The price is NZ$565
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Country Cottage #3
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 NZ$285
includes taxes & fees
27 Dec - 28 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
10.0 out of 10, Exceptional, (61)
"Super friendly host. Incredibly easy to navigate to. Great little place for my visit. Very walkable to where I was visiting. Loved the stay, will be booking again. "
United States
Dan
Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!
6.8 out of 10, (26)
"Well kept. Small yet comfortable."
United States
Aimee W.
The price is NZ$392
includes taxes & fees
1 Jan - 2 Jan 2026
Walk to Beach 2BR Near Dining & Shopping

Holiday Home in Bay Shore

LUXURY BAY SHORE HOME
2.0 star property
2.0 out of 10, (2)
"DO NOT book this house! I booked this house for Thanksgiving day visiting family. I received confirmation and everything. However till the day of arrival I never received any instruction on checking in. I called multiple times and only got voice mail in spanish. Finally I received a message saying this house was no longer available several hours before checking in! We had to scramble to find hotel rooms for 10 people. It was totally unacceptable!"
United States
Yan
LUXURY BAY SHORE HOME
10.0 out of 10, Exceptional, (10)
"Super enjoyable."
United States
Arlene K.
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Apartment in Central Islip

Cozy 2 bedroom retreat in long island
2.0 star property
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 NZ$431
includes taxes & fees
11 Jan - 12 Jan 2026
Cozy 2 bedroom retreat in long island
9.0 out of 10, Wonderful, (32)
"This unit was great. It's clean, quiet, and centrally located. It comes with 2 bikes which is a huge bonus (the rentals down the street are 40/day). It also has beach chairs and towels which is nice. We would definitely stay here again. "
United States
Kevin E.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck
9.8 out of 10, Exceptional, (73)
"This adorable cottage has everything you could want our need. 15/10 stars."
United States
Cindy
Adorable Cottage with Water Views, Across the street from Prime & other eateries
9.6 out of 10, Exceptional, (21)
"It was nice to stay at this house that has alot of historic relavance to the area. "
United States
dennis b.
1856 Trading House close to water

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is NZ$830
includes taxes & fees
6 Jan - 7 Jan 2026
Captain's Cottage - Cold Spring Harbor Water Views
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 NZ$308
includes taxes & fees
20 Dec - 21 Dec
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
6.0 out of 10, (2)
"Very comfortable and welcoming Only problem was only one bathroom door closed the other one appeared to be in disrepair Other then that all was well"
United States
Kathleen
3 Bedroom Historic Home near Stony Brook Village, University, Hospital & Beaches
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.
Save an average of 15% on thousands of hotels when you're signed in

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 favorite 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 depends 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 NZ$285 per night. Entering your travel dates in the search wizard you might find 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.