Vacation rentals in Smithtown

The Suite at North shore LI

This unique place has a style all its own. We have created a combination of a peaceful atmosphere with a sophisticated touch. Few minutes away from Stony brook Hospital and University, and other educational and hospital destinations. Few minutes away to many of the best restaurants on the North Shore LI. And of course if you are visiting to just enjoy the Island, this is the perfect location to any desire destination like wineries, beaches and so many places this beautiful Island has to offer.

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

The Historic 1813 House

Recently restored, this Port Jefferson Village historic house has all of the amenities of today. Boasting 3 bedrooms and 2 full bathrooms, a short walk to the busy day and night life of Main Street. Watch the sunrise from the top bedroom over the port and watch ferry boats as they arrive throughout the day. Read a book in the beautiful all wood sitting room or take a bath in the recently restored cast iron claw foot tub. This house offers quiet serenity with an option to explore the village.

*NEW LUX Northshore River KING, privacy deck/yard

Welcome to the perfect private space to unwind and relax. This completely remodeled King Suite comes with all the conveniences you'll need for a great stay - plus some little touches that we hope make you feel special. The Northshore Corner Oasis, is a fine retreat where you can recharge your batteries and plan your exciting Long Island adventures. 1 block from the beautiful Riverfront, enjoy a short walk to the pizzeria or the bagel shop, or both! Plus, your well-behaved pet is welcome.

Tranquility Getaway, Private Luxe Suite & Backyard

🌿 Welcome to Tranquility Getaway — a luxurious retreat nestled in the heart of Smithtown. Indulge in our Modern Newly Designed 2-bedroom Private Basement Luxe Suite, located on the left side of the property with a short staircase leading to your exclusive entrance on the lower level. Unwind in your private outdoor haven, featuring refined seating for four, a stone-top fire pit, and a solar-lit umbrella. THIS IS NOT THE ENTIRE HOUSE‼️ PLEASE REVIEW 📸 PHOTOS & HOUSE RULES BEFORE BOOKING‼️

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!!

2 Bedroom Luxury Apartment

Welcome to our beautiful luxury 2 bed apt in kings park.This Apt features a full living room. The kitchen is fully functioning with all the amenities it’s well equipped. 1 bed has a fully adjustable bed with its own TV. plenty of storage. 2nd bed features has its own tv as well. Located just minutes away from st Catherine med complex, golf and fine dining, beautiful beaches and parks. P.S this 2nd story Apt see pics for staircase. Pls note the bathroom entrance is in the 1st bedroom.

Harborfront Star Walk to Harbor & Village

Leave your car parked , hang your keys, and step into the charm of Port Jefferson Village from this beautifully styled coastal retreat. Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.

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.

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.