Best Vacation Homes in Smithtown
Apartment
10.0(44 Reviews)
1 Bedroom
1 Bath
2 Guests
550 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
AU $172/Night
7 Nights - AU $1,205
Apartment
8.4(13 Reviews)
1 Bedroom
1 Bath
4 Guests
495.14 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
AU $134/Night
7 Nights - AU $941
Hotel
8.8(395 Reviews)
1 Bath
- Fireplace/Heating
Breakfast- Kitchen
- Parking
AU $304/Night
7 Nights - AU $2,124
Apartment
10.0(19 Reviews)
1 Bedroom
1 Bath
2 Guests
Oceanfront- Fireplace/Heating
Ocean View- View
AU $239/Night
7 Nights - AU $1,676
House
8.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
3003.13 ft²
- Fireplace/Heating
Pool- View
Pet Friendly
AU $1,065/Night
7 Nights - AU $7,458
Apartment
10.0(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $544/Night
7 Nights - AU $3,805
Cottage
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
AU $378/Night
7 Nights - AU $2,647
Apartment
9.8(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
AU $232/Night
7 Nights - AU $1,627
Smithtown Luxury Rentals
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
3000 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
AU $1,534/Night
7 Nights - AU $10,737
House
9.4(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
600 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
AU $654/Night
7 Nights - AU $4,580
New
Apartment
10.0(3 Reviews)
4 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
AU $474/Night
7 Nights - AU $3,318
AU $369/Night
7 Nights - AU $2,581
Hotel
8.4(54 Reviews)
8 Baths
441.32 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Breakfast
AU $322/Night
7 Nights - AU $2,256
Apartment
7.6(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
AU $253/Night
7 Nights - AU $1,770
Hotel
6.3(122 Reviews)
1 Bath
301.39 ft²
- Air Conditioner
- Internet
Child Friendly
AU $166/Night
7 Nights - AU $1,162
House
5 Bedrooms
6 Baths
10 Guests
5300 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
AU $11,246/Night
7 Nights - AU $78,722
Smithtown Pet Friendly Vacation Rentals
Apartment
1 Bedroom
1 Bath
2 Guests
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
AU $210/Night
7 Nights - AU $1,472
House
5 Bedrooms
5 Baths
10 Guests
5300 ft²
Hot Tub- Fireplace/Heating
- Pool
- Pet Friendly
AU $9,128/Night
7 Nights - AU $63,899
Smithtown Top Rated Vacation Rentals
Apartment
5.0(1 Review)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Pool
- Kitchen
- Internet
AU $220/Night
7 Nights - AU $1,539
House
4 Bedrooms
2 Baths
8 Guests
3000 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
AU $7,651/Night
7 Nights - AU $53,556
Why Choose Rent By Owner for your Smithtown Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Smithtown
When should you plan your Vacation Rentals stay?
Knowing the best time to visit here can help you maximize your experience and enjoy the region's unique charms when the conditions are ideal for your vacation plans.
Peak Season Highlights
Summer (June to August)
The warm weather and longer days make this period ideal for exploring the area's scenic outdoors and enjoying local activities.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
This season offers vibrant foliage and pleasant temperatures, perfect for outdoor pursuits and experiencing the region's natural beauty.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
Experience a quieter atmosphere with cooler temperatures, making it suitable for cozy stays and off-season exploration.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F
Spring (March to May)
As the region awakens from winter, you'll enjoy fewer crowds and mild temperatures, ideal for those seeking a peaceful retreat.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Smithtown
How to Book Your Smithtown Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Smithtown
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with a well-maintained backyard for relaxing or entertaining under the sun.
- Take advantage of a spacious patio or deck fully equipped for outdoor dining and social gatherings.
- Make use of a barbecue grill to enhance your alfresco meals during your stay.
- Stay active with access to tennis courts, golf courses, or other sports facilities in the area.
- Discover scenic walking trails or hiking paths nearby that showcase the natural beauty of this destination.
- Relax by a swimming pool, perfect for cooling off during warm summer days in the region.
- Utilize outdoor lighting features to enjoy evening gatherings and star-gazing in the peaceful surroundings.
Top Attractions Around Smithtown
What attractions are nearby?
In this destination, you can enjoy a variety of outdoor activities and explore local parks just moments from your vacation rentals, making it easy to experience the natural beauty and recreational opportunities that the area has to offer.
Family Activities
- Smithtown Museum & Historical Society: Discover local history and engage your family with interactive exhibits at this enriching destination in the area.
- Nissequogue River State Park: Enjoy outdoor adventures such as hiking, picnicking, or paddleboarding along the scenic riverfront in this peaceful region.
- The Children's Museum of the South Shore: Foster creativity and learning through hands-on exhibits that are perfect for young children visiting here.
- Long Island Maritime Museum: Explore maritime history, including boat exhibits and educational programs, ideal for family members interested in the area's seafaring heritage.
Adult Activities
- Visit the Smithtown Historical Society Museum: Dive into the area's rich history and explore local exhibits that provide insight into the region's heritage.
- Enjoy outdoor activities at Caleb Smith State Park Preserve: Take a hike or have a relaxing picnic in this scenic park offering natural beauty just minutes from your stay.
- Play a round at the Smithtown Landing Country Club: Experience top-tier golfing surrounded by picturesque views, perfect for leisure and recreation.
- Discover local art and culture at nearby galleries: Engage with the regional arts scene and find unique pieces that reflect the area's creative spirit.
Other Places to Stay in Smithtown, NY
St. Catherine Of Siena Medical Center
Stonebridge Golf Links and Country Club
Blydenburgh County Park
Village of the Branch
Caleb Smith State Park
Smithtown Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's diverse eateries to enjoy authentic flavors and support local businesses during your stay.
- Plan Outdoor Activities: Utilize nearby parks and natural spots for outdoor adventures that let you experience the region's scenic beauty firsthand.
- Visit Seasonal Events: Check out the calendar for special events or festivals happening locally to immerse yourself in the area's vibrant community spirit.
- Coordinate Transportation in Advance: Arrange reliable transportation options to easily access key attractions and amenities, making your trip more convenient and enjoyable.
Transportation Options
- Long Island Rail Road: This regional train service offers convenient transportation options connecting you to New York City and other parts of Long Island from local stations near your vacation rentals.
- Personal Vehicle: Having a car provides flexibility to explore the area and access neighboring attractions with ease, especially when staying in the region's well-connected vacation rentals.
- Bus Services: Local bus routes serve the area, making it simple to get around without a vehicle while enjoying the comfort and affordability they offer to visitors here.
- Taxis and Rideshare Services: On-demand taxis and rideshares deliver quick, reliable transportation directly to your vacation rental, ensuring seamless travel within and beyond the region.
Local Customs Options
- Local Seafood Festivals: Participating in seasonal seafood festivals here allows you to enjoy fresh catches while experiencing the area's coastal traditions.
- Community Parades: Watching or joining community parades gives insight into the region's festive spirit and local heritage during special occasions.
- Traditional Sunday Dinners: Embracing family-centric Sunday dinners at local eateries offers a taste of authentic regional hospitality and culinary customs.
- Historical Celebrations: Attending local historical celebrations helps you appreciate the area's rich past and its influence on modern customs.
Frequently Asked Questions About Smithtown?
1. What are the top vacation rentals in Smithtown?
There are a lot of options in Smithtown. If you plan on staying in the Smithtown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Smithtown:
- Snow Birds, Transitions, Temporary Work Assignments, This is it!
- Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
- Tranquil & Pet-Friendly Estate on Long Island!
- Updated top level apartment - modern design with open floor plan
- Cozy Riverside Cottage
- Cozy 3BR Apartment in Peaceful Neighborhood With Kitchenette
- The Suite at North Shore Long Island, Prime Location, Unique and sophisticated
- Lovely escape, home away from home 10 mins from all beaches.
- Residence Inn By Marriott Long Island Hauppauge
- Residence Inn Long Island Hauppauge/Islandia
2. Which vacation homes in Smithtown are best for families?
If you are looking for a family-friendly vacation home in Smithtown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Smithtown:
3. How many Rentbyowner vacation rentals are available in Smithtown?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 24 in the Smithtown area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Smithtown.
4. What is the cancellation policy for vacation rentals in Smithtown, New York?
Cancellation policies vary depending on the property listing. You should review the specific cancellation terms outlined by the owner before booking to understand any potential fees or restrictions.
5. How do I contact the property owner if I have questions about my stay in this area?
You can reach out directly to the property owner through the messaging platform provided on the booking site. They can provide detailed information about the vacation rental and address any special requests or concerns.
6. Are there any additional fees or charges when booking a vacation rental here?
Additional fees such as cleaning, service charges, or local taxes may apply. These details are typically disclosed during the booking process, so review the listing carefully for complete pricing information.
7. What amenities are usually included with vacation rentals in this region?
Most listings include essential amenities like Wi-Fi, parking, and kitchen facilities, but it’s important to read each description to confirm which features are offered at your chosen property.
8. Is there a minimum stay requirement for vacation rentals in this destination?
Minimum stay requirements depend on the individual property; some listings may require a certain number of nights. Check the specific property details or contact the owner for this information before booking.
