Discover Your Perfect Upton Vacation Homes

Upton Pet Friendly Vacation Rentals

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Upton Large Vacation Homes

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Why Choose Rent By Owner for your Upton Vacation Rental Homes?

What makes our Vacation Rentals 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 Upton

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation here in Upton, Shirley, New York, ensures you can fully enjoy the area's charming atmosphere and natural beauty, making your stay truly memorable and tailored to your preferences.

Peak Season Highlights

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Summer (June to August)

During the summer months, you’ll enjoy warm weather perfect for outdoor activities and exploring the natural beauty of the region. This is when the area experiences its highest visitor influx, making it an ideal time for those seeking lively atmosphere and vibrant local events.

Average Temperature Daytime: around 80°F to 85°F - Nighttime: approximately 60°F to 65°F
autumn
Fall (September to November)

Autumn brings mild temperatures and stunning fall foliage, creating a picturesque setting for outdoor adventures and scenic drives. The region sees a surge in visitors who come to enjoy the colorful landscape and seasonal festivities.

Average Temperature Daytime: about 65°F to 70°F - Nighttime: roughly 45°F to 50°F

Off-Season Highlights

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Winter (December to February)

You might experience quieter days during the winter season, with cooler temperatures making it perfect for cozy stays in your vacation rental. This period attracts fewer travelers, providing a peaceful retreat here away from the crowds.

Average Temperature Daytime: around 35°F to 40°F - Nighttime: close to 25°F to 30°F
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Spring (March to May)

Spring offers mild weather and blooming landscapes, though this shoulder season tends to see fewer visitors. It’s an excellent time for those seeking a tranquil visit and fresh natural scenery without the peak-season prices.

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

Weekly Weather Forecast for Upton

How to Book Your Upton 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 Upton

More Top-Rated Vacation Rentals in Upton Area

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 outdoor dining with a fully equipped barbecue grill, perfect for gatherings in the region's pleasant weather.
  • Relax by a private pool or hot tub to unwind after exploring the scenic surroundings of this area.
  • Take advantage of spacious patios or decks that offer stunning views and comfortable seating options.
  • Utilize well-maintained gardens or landscaped yards ideal for outdoor activities or picnics nearby.
  • Benefit from dedicated outdoor fire pits, great for cozy evenings under the stars.
  • Make use of parking spaces designed for convenience when arriving in this destination.
  • Explore nearby hiking or nature trails accessible directly from your rental’s outdoor space, immersing yourself in the area's natural beauty.

Top Attractions Around Upton

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and local attractions that make your stay in Upton, Shirley, New York a memorable experience.

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Family Activities

  • Long Island Game Farm Wildlife Park & Children's Zoo: Spend a fun-filled day exploring this local wildlife park, where your family can enjoy interactive animal exhibits and learn about conservation efforts in the region.
  • Cedar Beach County Park: Relax and play on the sandy shores of this popular beach, perfect for swimming, picnicking, or building sandcastles with your loved ones during your stay.
  • Shirley Historical Society Museum: Discover the local history through engaging exhibits and guided tours that provide insight into the area's past, ideal for family educational outings.
  • William Floyd Estate: Explore the historic site offering outdoor activities and interpretive programs that give your family a glimpse into the colonial era here in Suffolk County.
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Adult Activities

  • Wine Tasting Tours: Explore local vineyards and enjoy guided wine tasting experiences amid the scenic landscapes of the region.
  • Golfing at a Championship Course: Spend your day on pristine fairways at a nearby golf course, perfect for both beginners and seasoned players.
  • Hiking in Nature Reserves: Discover stunning trails and diverse wildlife while hiking through protected areas around here.
  • Fishing Expeditions: Cast your line in lakes and rivers known for their excellent fishing opportunities in this part of New York.

Other Places to Stay in Upton, NY

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Upton Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the area's scenic outdoor spaces to enjoy peaceful walks or hikes that highlight the natural beauty surrounding your rental in this part of New York.
  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times can help you experience the region's serene atmosphere and secure more exclusive access to local attractions and amenities.
  • Connect with Community Events: Engage with local happenings to immerse yourself in the regional culture, making your stay more memorable and authentic.
  • Pack Appropriately for the Climate: Check the weather forecast before your trip to ensure you bring suitable clothing, allowing you to fully enjoy outdoor activities and explore comfortably.

Transportation Options

  • Long Island Rail Road (LIRR): This regional rail service provides convenient access to New York City and other parts of Long Island from nearby stations, making it easy to explore the region without a car.
  • Local Bus Services: The area is served by several bus routes that connect you to key destinations within Suffolk County, offering an affordable and flexible transportation option.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily available, providing quick and direct transportation around here, especially for short trips or those arriving at local airports.
  • Private Car Rentals: Renting a car locally allows you to explore the region at your own pace, with numerous rental agencies offering vehicles suitable for any travel plans in this destination.

Local Customs Options

  • Traditional Italian Cuisine: Locals often gather to enjoy authentic Italian dishes, reflecting the area's rich cultural heritage.
  • Community Celebrations: Community events and parades are a cherished tradition, fostering a strong sense of unity among residents.
  • Respect for Nature: Many here observe a deep respect for the natural surroundings, emphasizing outdoor activities and conservation efforts.
  • Local Artisans: Supporting local artisans and their handcrafted goods is a common custom, showcasing the area's artistic spirit.

Frequently Asked Questions About Upton?

1. What are the top vacation rentals in Upton?

There are a lot of options in Upton. If you plan on staying in the Upton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Upton:

2. How many vacation rentals have private pools in Upton?

There are 8 vacation rentals with private pools near Upton. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Upton are best for families?

If you are looking for a family-friendly vacation home in Upton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upton:

4. How many Rentbyowner vacation rentals are available in Upton?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 97 in the Upton 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 Upton. 

5. What is the cancellation policy for vacation rentals in the area?

The cancellation policies vary depending on the property. You should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees.

6. Are there any house rules I should be aware of before booking?

Each vacation rental has its own set of house rules, which are outlined in the listing. Make sure to read these carefully to ensure your stay complies with the owner's requirements.

7. How do I confirm the availability of a rental during my travel dates?

Availability can be checked through the listing calendar. If you have specific dates in mind, contacting the property owner directly can also help verify if the property is available for your intended stay.

8. What amenities are typically included in vacation rentals here?

Amenities vary by property but often include essentials like Wi-Fi, parking, kitchen facilities, and sometimes additional features such as outdoor spaces or entertainment options. Review each listing's amenities section for precise details.

9. Is it possible to make special requests or accommodations when booking a vacation rental?

Yes, many owners are willing to consider special requests. It's best to reach out directly to the property owner before booking to discuss any specific needs or preferences.