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Smithtown Holiday Rentals

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Holiday Rentals in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

5.0 out of 10, (2)
"Overall clean space and super easy check in/out. Location is on a quiet street/neighborhood which is nice. Not full a/c in rooms but had two floor fans; was hot in summertime but manageable for a short stay. Had a nice deadbolt on door to lock it. Awkward entrance as you go through the back of the house and all the way around the property, but it isn't terrible. A bit of a dead zone for Verizon but T-mobile was OK; Wi-Fi was available which was needed. Good for easy overnight stay and cheaper...
The price is NZ$390
includes taxes & fees
19 Sept - 20 Sept
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (69)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is NZ$545
includes taxes & fees
14 Sept - 15 Sept
Guesthouse at Norwalk Inn

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is NZ$619
includes taxes & fees
1 Oct - 2 Oct
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (69)
"Very nice place for a family to stay"
The price is NZ$2,158
includes taxes & fees
29 Sept - 30 Sept
Newly Renovated Luxury Beach House Ocean Bay Park

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (19)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

9.2 out of 10, Wonderful, (15)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is NZ$254
includes taxes & fees
13 Sept - 14 Sept
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

9.4 out of 10, Exceptional, (26)
"its small but very nice for a short stay would recommend."
The price is NZ$279
includes taxes & fees
9 Sept - 10 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

1 bed room basement apartment.

8.2 out of 10, Very good, (10)
"The property was very spacious and can bring family there. "
The price is NZ$284
includes taxes & fees
9 Sept - 10 Sept
1 bed room basement apartment.

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

9.4 out of 10, Exceptional, (6)
"Had a great stay "
The price is NZ$265
includes taxes & fees
12 Sept - 13 Sept
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

2.0 out of 10, (1)
"While we received multiple confirmations of our reservation, including the morning we were to check in, the property manager never sent us check in instructions, even after we emailed asking for them. Then, after spending over an hour with multiple calls to VRBO customer service, who also couldn’t get ahold of the property manager, we arrived at the location. There was a 4ft high, 10ft wide heap of garbage in the front yard and looking in through the windows it was apparent the house was under...
The price is NZ$1,813
includes taxes & fees
15 Sept - 16 Sept
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.8 out of 10, Exceptional, (8)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is NZ$2,008
includes taxes & fees
18 Sept - 19 Sept
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

9.8 out of 10, Exceptional, (21)
"Great time...close to the beach or the bay"
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

Tiny Home Private, Students, Nurses, Tech

9.4 out of 10, Exceptional, (3)
"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!"
The price is NZ$336
includes taxes & fees
9 Sept - 10 Sept
Tiny Home Private, Students, Nurses, Tech

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is NZ$517
includes taxes & fees
9 Sept - 10 Sept
Walk to Beach 2BR Near Dining & Shopping

Chic Private 1BR Suite/Walk to Shops

9.0 out of 10, Wonderful, (2)
"Vanessa is very responsive and laid back. She made the booking and check-in process seamless and the location of her property is stellar. The neighborhood is great to walk dogs and safe. "
The price is NZ$485
includes taxes & fees
9 Sept - 10 Sept
Chic Private 1BR Suite/Walk to Shops

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is NZ$1,069
includes taxes & fees
9 Sept - 10 Sept
Modern Vacation home. Close to The Hamptons

1 bedroom 1 bath private entrance

8.8 out of 10, Excellent, (20)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
The price is NZ$351
includes taxes & fees
9 Sept - 10 Sept
1 bedroom 1 bath private entrance

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
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

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 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?

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.: This holiday home rental outside of Smithtown has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.