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Holiday Rentals in Smithtown

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Holiday Rentals in Smithtown

Our top choices for Smithtown holiday rentals

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

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (68)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach

“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 €320
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, (67)
"Very nice place for a family to stay"
The price is €1,113
includes taxes & fees
29 Sept - 30 Sept
Newly Renovated Luxury Beach House Ocean Bay Park

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 €145
includes taxes & fees
2 Sept - 3 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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

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 €275
includes taxes & fees
7 Sept - 8 Sept
Guesthouse at Norwalk Inn

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (58)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

9.4 out of 10, Exceptional, (6)
"Had a great stay "
The price is €138
includes taxes & fees
7 Sept - 8 Sept
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

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 €266
includes taxes & fees
2 Sept - 3 Sept
Walk to Beach 2BR Near Dining & Shopping

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!

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

The price is €970
includes taxes & fees
7 Sept - 8 Sept
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

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!

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 €270
includes taxes & fees
15 Sept - 16 Sept
Chic Private 1BR Suite/Walk to Shops

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 €173
includes taxes & fees
2 Sept - 3 Sept
Tiny Home Private, Students, Nurses, Tech

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (13)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

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

Charming 4 bedroom home with pool, basketball court, in superb East Patchogue

10.0 out of 10, Exceptional, (1)
"Nice house and great pool. "
The price is €2,544
includes taxes & fees
30 Sept - 1 Oct
Charming 4 bedroom home with pool, basketball court, in superb East Patchogue

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (48)
"We've stayed here twice when visiting family in town, it's a lovely space and very welcoming."
1856 Trading House w/ walk to water

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 €132
includes taxes & fees
2 Sept - 3 Sept
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
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, apart-hotels, 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 €132 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 a Smart TV 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.