Smithtown Holiday Rentals

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Our top choices for Smithtown holiday rentals

6.8 out of 10, (3 reviews)
"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.
The price is NZ$385
includes taxes & fees
22 Mar - 23 Mar
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
7.0 out of 10, Good, (4 reviews)
"Super convenient and the host was very responsive. I highly recommend."
United States
Andrew B.
The price is NZ$390
includes taxes & fees
2 Apr - 3 Apr
Lovely RV with AC in charming Bethpage a mile from the train to NYC
8.6 out of 10, Excellent, (7 reviews)
"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 NZ$365
includes taxes & fees
26 Mar - 27 Mar
Tiny Home Private, Students, Nurses, Tech
3.0 star property
The price is NZ$855
includes taxes & fees
23 Mar - 24 Mar
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic! Well communicated and perfectly described! Highly recommend and thank you!"
United States
Wayne L.
The price is NZ$304
includes taxes & fees
2 Apr - 3 Apr
Your Perfect Getaway Between Farmingdale & Amityville
8.8 out of 10, Excellent, (10 reviews)
"This stay was private and comfortable. Checking in was easy with an electronic lock and the host was very communicative with my questions. 2 things to note are that the walls are thin between this unit and the main house so you can indistinctly hear each other, and the mattress is quite hard, but I know some people prefer that. The bathroom is modern and clean and overall everything was easy. "
United States
Zoe P.
The price is NZ$278
includes taxes & fees
22 Mar - 23 Mar
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (75 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is NZ$831
includes taxes & fees
30 Mar - 31 Mar
Captain's Cottage - Cold Spring Harbor Water Views
7.8 out of 10, Good, (10 reviews)
"The host was extremely attentive to any questions or needs. Excellent and immediate communication. Good, quiet location between Islip airport and Port Jefferson. The size of the unit was very adequate for two people. Bathroom was clean and adequately stocked with towels and wash cloths.The reason for 2 stars is we thought the apartment was not very clean from floor to ceiling. This apartment has huge potential to be very cute. In my option, it needs an entire over haul."
United States
Russell R.
The price is NZ$575
includes taxes & fees
23 Mar - 24 Mar
Spacious one Bedroom Apt with private entrance

Apartment in Mastic

South Shore Studio in Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is NZ$386
includes taxes & fees
22 Mar - 23 Mar
South Shore Studio in Mastic

Holiday Home in Ronkonkoma

The Royal Suite - Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is NZ$671
includes taxes & fees
24 Mar - 25 Mar
The Royal Suite - Ronkonkoma
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is NZ$915
includes taxes & fees
23 Mar - 24 Mar
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is NZ$307
includes taxes & fees
31 Mar - 1 Apr
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (3 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$635
includes taxes & fees
23 Mar - 24 Mar
Luxe Provincial Style Studio w/ Patio & Parking
9.4 out of 10, Exceptional, (39 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
The price is NZ$280
includes taxes & fees
2 Apr - 3 Apr
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is NZ$873
includes taxes & fees
28 Mar - 29 Mar
Modern Vacation home. Close to The Hamptons

Apartment in Huntington Station

THE OASIS @ LONG ISLAND
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is NZ$821
includes taxes & fees
22 Mar - 23 Mar
THE OASIS @ LONG ISLAND
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is NZ$1,612
includes taxes & fees
22 Mar - 23 Mar
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Holiday Home in Historic District

Family Cottage with 4 King Beds and Fire Pit
10.0 out of 10, Exceptional, (10 reviews)
"Clean and host was very helpful and accommodating. Highly recommend! "
United States
Brenna M.
The price is NZ$893
includes taxes & fees
25 Mar - 26 Mar
Family Cottage with 4 King Beds and Fire Pit

Apartment in Bay Shore

1 bedroom 1 bath private entrance
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is NZ$282
includes taxes & fees
2 Apr - 3 Apr
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

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$280 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?

Spacious Home Located Close to Stony Brook!: This holiday home rental outside of Smithtown offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.