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  2. New York
  3. Smithtown
  4. Rentals by Owner

Smithtown Rentals by Owner

8.3 (7 Reviews)
Apartment
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Why Choose Rent By Owner for your Smithtown vacation rental?

What makes our Rentals by Owner special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Rentals by Owner stay?

To make the most of your stay, consider visiting during the optimal seasons when the area's weather and local events provide a truly memorable experience, ensuring that your rental by owner in Smithtown offers both comfort and convenience at the perfect time.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, this area experiences its peak season, making it ideal for outdoor activities and enjoying the local scenery.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
autumn
Fall (September to November)

The region's autumn months attract visitors who seek pleasant weather and vibrant foliage, creating a lively atmosphere for travelers in this destination.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December to February)

In winter, the area sees fewer visitors, offering a quieter experience and potentially better deals on vacation rentals by owner.

Average Temperature Daytime: 30°F to 45°F - Nighttime: 20°F to 30°F
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Spring (March to May)

Early spring brings shoulder season pricing and less crowds, perfect for those looking to explore with more tranquility in the region.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Smithtown

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.

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 swimming pool to relax and cool off during your stay.
  • Take advantage of spacious patios or decks perfect for outdoor dining and entertaining.
  • Make the most of lush, landscaped yards ideal for outdoor activities or simply unwinding in the fresh air.
  • Utilize designated grilling areas or outdoor kitchens to prepare meals al fresco.
  • Benefit from outdoor fire pits or fireplaces for cozy gatherings on cooler evenings.
  • Access scenic garden spaces or walking trails for outdoor exploration and leisure.
  • Experience the convenience of covered porches or gazebos, providing shade and shelter when enjoying the sunny region.
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Family Activities

  • Long Island Aquarium: Discover a fascinating marine world where your family can explore interactive exhibits and enjoy engaging animal demonstrations.
  • Sagtikos Manor and Park: Step back in time at this historic site offering scenic outdoor spaces perfect for picnics and family walks in the region’s rich history.
  • The Smithtown Historical Society Museum: Engage your family with local history through informative exhibits and educational programs that bring the area's past to life.
  • Nissequogue River State Park: Experience outdoor adventure with kayaking, fishing, and nature trails along this peaceful river setting in the nearby area.
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Adult Activities

  • Visit the Smithtown Historical Society: Immerse yourself in the local history of this area by exploring exhibits and collections that showcase its rich heritage.
  • Enjoy a round of golf at the Smithtown Golf Course: Relax and unwind with a scenic game on the well-maintained greens nestled within the region.
  • Explore Sunken Meadow State Park: Experience outdoor recreation with hiking, picnicking, or beach activities along the waterfront of this popular park.
  • Discover local arts at the Contemporary Arts Center: Engage with the regional art scene by viewing exhibitions and participating in creative workshops here in the vicinity.

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?

  • Plan Your Activities in Advance: Research local events and attractions to make the most of your stay here and choose nearby rental options that suit your interests.
  • Select a Convenient Location: Opt for a rental close to key amenities and transportation routes in this area to maximize your exploration time.
  • Engage with Local Hosts: Communicate with your host beforehand to get insider tips on hidden gems and the best dining experiences in the region.
  • Check Amenities Carefully: Ensure your chosen rental offers essential comforts and facilities to enjoy a relaxing and hassle-free visit in this destination.

Transportation Options

  • Long Island Rail Road (LIRR): You can access reliable train services connecting here to New York City and other parts of Long Island, making commutes seamless across the region.
  • Local Bus Services: Public bus routes serve the area extensively, providing an affordable and convenient way to explore local destinations and nearby towns.
  • Car Rentals: Renting a vehicle is an ideal option for flexibility and comfort when navigating this destination and exploring surrounding areas at your own pace.
  • Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available here, offering quick and direct transportation throughout the region.

Local Customs Options

  • Local Farming Traditions: Here, you can experience the region's rich agricultural heritage that influences local markets and seasonal festivals.
  • Community Festivals and Parades: The area hosts annual events that celebrate its history and creativity, providing a glimpse into local customs and community spirit.
  • Traditional Seafood Dining Etiquette: With access to fresh catches from nearby waters, understanding dining customs enhances your culinary experience here.
  • Historical Preservation Practices: Respect for historic landmarks and architecture is a key aspect of the area's cultural identity, often reflected in local tours and community events.

Frequently Asked Questions About Smithtown Rentals by Owner

1. How many Rentbyowner vacation rentals are available in Smithtown?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 18 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. 

2. What is the cancellation policy for rental properties in Smithtown, New York?

Cancellation policies vary by listing. To find the specific details, please refer to the property’s listing or contact the owner directly before booking.

3. How do I contact the owner of a rental in Smithtown for special requests or questions?

You can reach out to the owner through the messaging system provided on the Rent By Owner platform. For any urgent inquiries, it’s best to contact them prior to completing your reservation.

4. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or security deposits are specified in each listing. Review the details carefully on the listing page before confirming your reservation.

5. What is the check-in and check-out process for rentals in the area?

Check-in and check-out procedures are detailed in each listing. Owners typically provide instructions upon booking confirmation, and it’s recommended to follow their guidelines for a smooth stay.

6. Is there a minimum stay requirement for booking a rental here?

Minimum stay requirements vary depending on the property and season. Please review the specific listing for this information or contact the owner if you have special scheduling needs.