Holiday houses in Smithtown

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Top-rated holiday rentals in Smithtown

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Guest favourite

Apartment in Port Jefferson Station

4.97 out of 5 average rating, 144 reviews

All Private Bright Spacious Close to All

DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -queen sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

25 Feb – 4 Mar

$255 NZD per night

Guest favourite

Apartment in Huntington

4.97 out of 5 average rating, 219 reviews

Historic Huntington Village Private Retreat

50 min from NYC on LIRR to Huntington. Less than one mile from the train station and an easy walk to Huntington village in an historic, vibrant, relaxed and unique neighborhood. Plenty to do in the area with many parks and beaches and a great place to enjoy nature. It is a short walk (a half mile) to Huntington village where there are many great restaurants, bars, and shops, plus the Paramount Theater. This stylish comfortable place is clean, cozy and quiet. Sorry, no pets allowed, dander-free!

5–12 Nov

$239 NZD per night

Guest favourite

Apartment in Stony Brook

4.99 out of 5 average rating, 128 reviews

Home Away From Home To SBU & SB Hospital

Stay in our private studio apartment that has the vibe of warmth and serenity. It is situated in a quiet neighborhood of Stony Brook with beautiful tree-lined streets. The studio has a warm and rustic feel and detailed amenities to make your visit a pleasure. It is perfect for someone traveling for business at Stony Brook Hospital or for parents or grandparents of a student attending Stony Brook University (5 minutes). It is great for couples attending a wedding at the Harbor or nearby towns.

26 Jan – 2 Feb

$242 NZD per night

Guest favourite

Apartment in Deer Park

4.97 out of 5 average rating, 112 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

12–19 Nov

$215 NZD per night

Guest favourite

Apartment in Smithtown

4.98 out of 5 average rating, 183 reviews

Mimi's Retreat -Private street level basement apt.

Walk-in street level one bedroom basement apartment with keypad entry in a quiet, safe neighborhood. Fully equipped kitchen includes cooking essentials, microwave, air fryer, electric tea kettle, Keurig coffee machine and toaster. Premium cable TV, excellent 5G Wi-Fi and Smart TV. Free parking on premise. Outside Security Camera's. Within walking distance to LIRR, restaurants and shopping. Centrally located between NYC, LI beaches & North Fork wine country. *NO PETS and NO SMOKING +

14–21 Feb

$297 NZD per night

Guest favourite

Home in Holbrook

4.91 out of 5 average rating, 236 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

19–26 Jun

$187 NZD per night

Guest favourite

Apartment in Stony Brook

4.78 out of 5 average rating, 544 reviews

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

14–21 Aug

$254 NZD per night

Guest favourite

Guest suite in Stony Brook

4.95 out of 5 average rating, 109 reviews

Cozy cottage in a charming historic village!

Our guest suite is perfectly located in the Old Historic District of Stony Brook Village across from the duck pond. We are only a few steps away from Avalon Park and Preserve, Sand Street Beach, the Long Island Museum, restaurants and shops. The village offers numerous places to explore in our quaint town and even more day trips on the outskirts where you can enjoy the simple pleasures during your time at our relaxing cottage.

18–25 Aug

$343 NZD per night

Guest favourite

Apartment in Northport

4.92 out of 5 average rating, 129 reviews

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

13–20 Nov

$233 NZD per night

Superhost

Cottage in Kings Park

4.79 out of 5 average rating, 143 reviews

Cozy Riverside Cottage

This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.

4–11 Sep

$612 NZD per night

Guest favourite

Home in Ronkonkoma

4.86 out of 5 average rating, 147 reviews

Convenient home in Ronkonkoma

Charming cape that is completely private. This is not an apartment within a house. The entire home and yard are yours to enjoy with complete privacy. Conveniently located 6 blocks from LIRR Ronkonkoma Station, 2 miles from Islip MacArthur Airport, and 1 mile from Long Island Expressway. 5.5% Occupancy Tax included.

2–9 Jun

$214 NZD per night

Guest favourite

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 234 reviews

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

26 Oct – 2 Nov

$345 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Smithtown holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Smithtown's top sights

Maureen's Kitchen6 locals recommend

Insignia Prime Steak & Sushi4 locals recommend

Blydenburgh County Park5 locals recommend

Cafe Havana3 locals recommend

Uncle Giuseppe's Marketplace7 locals recommend

Sangria 715 locals recommend

Other great holiday rentals in Smithtown

Guest favourite

Apartment in Patchogue

4.88 out of 5 average rating, 148 reviews

1 Bedroom Apartment on Long Island

26 Aug – 2 Sep

$209 NZD per night

Guest favourite

Apartment in Islip Terrace

4.99 out of 5 average rating, 138 reviews

Near all! - Full Kitchen, Backyard & Fire Pit!

18–25 Feb

$291 NZD per night

Guest favourite

Cottage in Patchogue

4.95 out of 5 average rating, 202 reviews

Quaint Cottage on Long Island's South Shore.

1–8 Feb

$269 NZD per night

Guest favourite

Apartment in Northport

4.95 out of 5 average rating, 191 reviews

NORTHPORT APARTMENT: Private, Clean, Cozy

23 Feb – 2 Mar

$343 NZD per night

Guest favourite

Guest suite in Smithtown

4.93 out of 5 average rating, 42 reviews

Bright 1-Bdrm Studio Apt on Quiet Tree-Lined St.

3–10 Jun

$259 NZD per night

Guest favourite

Guest suite in Kings Park

4.94 out of 5 average rating, 53 reviews

*NEW LUX Northshore River KING, privacy deck/yard

26 May – 2 Jun

$286 NZD per night

Guest favourite

Home in Ronkonkoma

4.9 out of 5 average rating, 29 reviews

The Ronkonkoma Bungalow

10–17 Sep

$277 NZD per night

Guest favourite

Apartment in Smithtown

4.88 out of 5 average rating, 16 reviews

Paradise on Long Island

10–17 Nov

$300 NZD per night

Show all

Quick stats about holiday rentals in Smithtown

Total rentals
40 properties
Local attractions
Watermill Caterers, Blydenburgh County Park and Maureen's Kitchen
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Total number of reviews
2K reviews

Holiday houses in Smithtown

Top-rated holiday rentals in Smithtown

Apartment in Port Jefferson Station

Apartment in Huntington

Apartment in Stony Brook

Apartment in Deer Park

Apartment in Smithtown

Home in Holbrook

Apartment in Stony Brook

Guest suite in Stony Brook

Apartment in Northport

Cottage in Kings Park

Home in Ronkonkoma

Guest suite in Lake Ronkonkoma

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Smithtown holiday rentals

Stay near Smithtown's top sights

Other great holiday rentals in Smithtown

Apartment in Patchogue

Apartment in Islip Terrace

Cottage in Patchogue

Apartment in Northport

Guest suite in Smithtown

Guest suite in Kings Park

Home in Ronkonkoma

Apartment in Smithtown

Quick stats about holiday rentals in Smithtown

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Rentals with dedicated workspaces

Total number of reviews

Destinations to explore