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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
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.
The price is NZ$397
includes taxes & fees
31 Oct - 1 Nov
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (74)
"Loved this venue! "
United States
adriano
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 "
United States
anthony
The price is NZ$511
includes taxes & fees
6 Nov - 7 Nov
Guesthouse at Norwalk Inn
Newly Renovated Luxury Beach House Ocean Bay Park
10.0 out of 10, Exceptional, (71)
"Very nice place for a family to stay"
United States
James K.
Newly Renovated Luxury Beach House Ocean Bay Park
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.6 out of 10, Exceptional, (32)
"This studio is so cute and cozy."
United States
Michelle H.
The price is NZ$285
includes taxes & fees
5 Nov - 6 Nov
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
10.0 out of 10, Exceptional, (87)
"Unbelievable house, gorgeous in person. The dock at the back if the property has beautiful views. So many luxury touches throughout the house. Stunning property. Would have loved to stayed longer."
United States
Jennifer S.
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
9.0 out of 10, Wonderful, (18)
"Clean and quiet little place convenient to many industrial parks. "
United States
Bradley C.
The price is NZ$261
includes taxes & fees
29 Oct - 30 Oct
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (70)
"Location was perfect!"
United States
Linda J P.
The price is NZ$817
includes taxes & fees
5 Nov - 6 Nov
Captain's Cottage - Cold Spring Harbor Water Views
1 bed room basement apartment.
8.4 out of 10, Very good, (11)
"The property was very spacious and can bring family there. "
United States
Manaelle
The price is NZ$290
includes taxes & fees
30 Oct - 31 Oct
1 bed room basement apartment.
Walk to Beach 2BR Near Dining & Shopping
6.8 out of 10, (23)
"Stay away"
United States
Alex H.
The price is NZ$404
includes taxes & fees
10 Nov - 11 Nov
Walk to Beach 2BR Near Dining & Shopping
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
9.2 out of 10, Wonderful, (12)
"This is a quiet and beautiful spot on the water. The outside space is perfect to relax or get some sun. The inside space was relaxing and very comfortable. The host, Richard was wonderful and very responsive. "
United States
Lori G.
The price is NZ$1,182
includes taxes & fees
29 Oct - 30 Oct
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Modern Vacation home. Close to The Hamptons
10.0 out of 10, Exceptional, (3)
"good time"
United States
Roy T.
The price is NZ$1,148
includes taxes & fees
3 Nov - 4 Nov
Modern Vacation home. Close to The Hamptons
Tiny Home Private, Students, Nurses, Tech
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 NZ$371
includes taxes & fees
29 Oct - 30 Oct
Tiny Home Private, Students, Nurses, Tech
Newly renovated Private bedroom near Stony Brook University
2.0 star property
6.0 out of 10, (1)
"A one family home still undergoing renovations to its kitchen, the property was clean and properly appointed for our one-night stay, which only required one bedroom, sheets and towels. "
United States
Rudolph
The price is NZ$401
includes taxes & fees
2 Nov - 3 Nov
Newly renovated Private bedroom near Stony Brook University
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
9.0 out of 10, Wonderful, (53)
"The location is superb, can’t do much better! Towards the end of the main strip for privacy but still right near the action that you come to Ocean Beach for. The rental was clean and stocked with essentials upon our arrival (definitely a life-saver) with the onsite washer/dryer a bonus!As for the property owner, I’m happy to report that this one is a pleasure… congenial, accommodating and professional from the start of the reservation process and onward.We are looking forward to returning next...
United States
Amy B.
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Beautiful historic home in Stony Brook!
2.0 star property
8.6 out of 10, Excellent, (19)
"House is well located and very comfortable.We enjoyed our stay at the home."
United States
Jim D.
Beautiful historic home in Stony Brook!
1 bedroom 1 bath private entrance
8.8 out of 10, Excellent, (22)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
United States
Rose S.
The price is NZ$340
includes taxes & fees
3 Nov - 4 Nov
1 bedroom 1 bath private entrance
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (11)
"IF I COULD COULD 10 STARS I WOULD, APARTMENT WAS CLEAN , EVERYTHING WORKED PROPERLY, WAS A PLEASURE"
United States
Thomas
The price is NZ$310
includes taxes & fees
3 Nov - 4 Nov
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck
9.0 out of 10, Wonderful, (32)
"Great location, cute property. My third time staying there. The experience would be meaningfully enhanced with some updated furnishings and cookware - especially the sofa in the living room and the furniture on the upstairs deck. Regarding cookware - a frying pan and spatula would be nice!"
United States
Will M.
One Bedroom Apt. in Ocean Bay Park with Rooftop Deck
LUXURY BAY SHORE HOME
2.0 star property
2.0 out of 10, (1)
The price is NZ$1,828
includes taxes & fees
7 Nov - 8 Nov
LUXURY BAY SHORE HOME
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 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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : 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 fridge, a microwave and a coffee maker.

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.