
Vacation rentals in Smithtown
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Smithtown
Guests agree: these stays are highly rated for location, cleanliness, and more.

Fire Island Pines: Studio Cabin
Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

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 -full 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.

Cozy studio w/ private entrance
Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area with a pull-out twin bed and seating - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

The Red Cottage Circa 1936
This cottage is a gem to be found! From the primary room to the charming loft, this cottage can sleep 6! There is a full working kitchen. For those who wish to do exploring, you will be centrally located on LI giving you great ease in using LI rail road (.5 mile) from cottage and Port Jeff Ferry (1mile)from cottage. There is a large fenced in yard with BBQ and outdoor seating if you wish to dine in. Dogs are allowed w/prior notice and a $65 pet fee. You won’t beat this value! Has it All!!

The Sunshine House
Enjoy your stay and visit the Bayard Cutting Arboretum, SUSA Orlin & Cohen Sports Complex, Robert Moses Beach; centrally located between The Hamptons Vineyard Wine Tours & Manhattan. This unique home was originally built in 1921 and has since undergone renovations with additions added to the original structure, including the three bedroom / bath guest wing with a private entrance from the main house. We provide beverages and continental breakfast. Please email us for more details!

Private Cabin in Multi Acre Park
I have a professional cleaning company come between all guests. The property is the only house on the street abutting several acres of wooded park land. Get the feeling of nature/privacy similar to being up state NY yet centrally located to Sunken Meadow Parkway, Northern State, LIE. Also near food stores and other essentials. 400 MBPS Internet connection for those who need a reliable internet connection for work! Living room has a pull out queen couch if a 3rd bed is needed.

Port Jefferson Convenient, Cozy and Chic!
Bright, modern, newly renovated and landscaped space can sleep up to 6! Countless amenities including a kitchen with dishwasher, full size refrigerator. 3 bedrooms, 2 full baths, and common living space. Great for boaters or attending events in Port Jefferson, Stony Brook or anywhere on Long Island. We are a 1 minute drive or 10 minute walk from Port Jefferson Harbor and Ferry Dock. Centrally located on LI for easy access to LI rail road and bus routes.

Private, clean, entire upstairs, newly decorated
Please join us in our newly decorated, disinfected, very clean rental. Enjoy the entire 2nd floor of our home w/Priv entrance in the heart of beautiful East Northport. This rental has a Priv. full bath and priv. livingroom withTV, refrigerator, and microwave. Our home is very close walking distance to train and restaurants. Just a short drive or bike ride to beaches, theater, hiking, kayaking, golf course, breweries, and wineries. Smart WiFi TV only.

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.

Quaint Cottage on Long Island's South Shore.
The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Charming “hotel inspired” Retreat
Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

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!
Popular amenities for Smithtown vacation rentals
Other great vacation rentals in Smithtown

Lovely 1-bedroom rental unit with indoor fireplace

Cozy 2-Story Stay Near SH Mall & Jake’s 58 Casino

The Suite at North shore LI

Ronkonkoma Residence by the Lake

Spacious Northport Studio

Cozy Modern Getaway

*NEW LUX Northshore River KING, privacy deck/yard

Luxury Apartment
When is the best time to visit Smithtown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,110 ZAR | R2,110 ZAR | R1,958 ZAR | R1,992 ZAR | R2,161 ZAR | R2,279 ZAR | R2,279 ZAR | R2,212 ZAR | R2,347 ZAR | R2,161 ZAR | R2,262 ZAR | R2,245 ZAR |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Frequently Asked Questions
How much does it cost to stay in apartment rentals in Smithtown?
Experience the best of Smithtown with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Smithtown?
Yes! Work meets play with ease at over 20 vacation rentals in Smithtown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Smithtown?
Make yourself at home in Smithtown by choosing from our most frequently booked neighborhoods. We have over 160 vacation rentals in Village of the Branch, over 90 vacation rentals in Kings Park, and over 130 vacation rentals in Nissequogue.
Do apartment rentals in Smithtown have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Smithtown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Smithtown have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Smithtown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Smithtown have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Smithtown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Smithtown have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Smithtown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Smithtown?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Smithtown

Total vacation rentals
Explore 30 vacation rentals in Smithtown

Nightly prices starting at
Smithtown vacation rentals start at R675 ZAR per night before taxes and fees

Verified guest reviews
Over 1,980 verified reviews to help you choose

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Smithtown vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Smithtown rentals

4.9 Average rating
Smithtown stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Washington Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Columbia University
- Brooklyn Bridge
- Central Park Zoo
- MetLife Stadium
- Yale University
- Bronx Zoo
- Grand Central Terminal
- Ohel Chabad-Lubavitch
- Yankee Stadium
- United Nations Headquarters
- Jones Beach
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Old Glory Park
- Fairfield Beach
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- Cooper's Beach, Southampton




