95+ Vacation Rentals & Holiday Homes in Smithtown |
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Smithtown Accommodations - Hotels & Rentals

About Smithtown Vacation Rentals

Discover More than 95 Incredible Getaway Rentals Available in Smithtown. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Smithtown.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Smithtown, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Smithtown. The Average Size of Places to Stay Near Smithtown is 675.03 ft², with Prices Averaging US $770 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Smithtown. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Smithtown

Type Count
Vacation Homes 38
Holiday Apartments 30
Cottages 3

Use these Quick Filters to Find a Vacation Rental in Smithtown

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Smithtown with Online Reservations.

Weather in Smithtown, NY

View the weather forecast for Smithtown before booking your Smithtown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities SmithtownGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World SmithtownGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Stonebridge Golf Links and Country Club
Caleb Smith State Park
Blydenburgh County Park
St. Catherine Of Siena Medical Center
Stony Brook University
Port Jefferson
Paramount Theater
Fairfield University
NYCB Theatre at Westbury
Lake Ronkonkoma
Norwalk Maritime Aquarium
Baseball Heaven
Oheka Castle
Tanger Outlets
Jones Beach State Park
Farmingdale State College
NYIT Old Westbury Campus
TWA Flight 800 International Memorial
Sunken Meadow State Park
Eisenhower Park

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Caleb Smith State Park 94 Properties
St. Catherine Of Siena Medical Center 80 Properties
Stonebridge Golf Links and Country Club 34 Properties
Blydenburgh County Park 34 Properties
Village of the Branch 27 Properties

Frequently Asked Questions About Smithtown?

What are the top hotels, lake houses & vacation rentals in Smithtown?

We provide an array of great vacation destinations in Smithtown. If you are looking to stay in or around the Smithtown area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Smithtown:

How many Hotels & Vacation Rentals have private pools in Smithtown?

We have 2 Hotels & Vacation Rentals featuring a private pool in and near Smithtown. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Smithtown is best for families?

Searching for a family-friendly getaway in Smithtown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Smithtown?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 95 in the Smithtown area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Smithtown.


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