1. USA
  2. California
  3. Temecula
  4. Winchester
  5. Rentals by Owner

Discover Your Perfect Winchester Rentals by Owner

Winchester Rentals by Owner

9.5 (9 Reviews)
House
Sundance Retreat
  • Air Conditioner
  • Parking
  • View
View Availability
|
9.0 (2 Reviews)
House
Western Horizon Home
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
More Top-Rated Rentals by Owner in Winchester Area

Why Choose Rent By Owner for your Winchester 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 Winchester

When should you plan your Rentals by Owner stay?

To make the most of your stay in Winchester, California, USA, it's important to consider the best times of year when the region offers ideal weather and local events, helping you choose the perfect moment to book your rental by owner through Rent By Owner for a seamless vacation experience.

Peak Season Highlights

spring
Spring (March to May)

During this period, the region experiences mild temperatures and blossoming scenery, making it an ideal time to enjoy outdoor activities and explore the local surroundings.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Fall (September to November)

Autumn offers comfortable weather with vibrantly changing foliage, providing a scenic backdrop for your stay in this destination's charming accommodations.

Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F

Off-Season Highlights

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Summer (June to August)

The warmest months bring higher temperatures and greater visitor numbers, perfect for those seeking lively local events and longer days in this area.

Average Temperature Daytime: 85-95°F - Nighttime: 65-75°F
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Winter (December to February)

During the cooler months, the area tends to be quieter, offering a peaceful retreat and lower rates for your vacation rental by owner here.

Average Temperature Daytime: 55-65°F - Nighttime: 40-50°F

Weekly Weather Forecast for Winchester

How to Book Your Winchester vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Winchester

More Top-Rated Rentals by Owner in Winchester Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 areas perfect for meals under the sun in this scenic region.
  • Take advantage of private patios or decks to relax while soaking in the surrounding landscape.
  • Make use of beautifully landscaped gardens that add charm to your vacation experience.
  • Benefit from access to community parks or outdoor recreational spaces nearby.
  • Utilize spacious yards ideal for outdoor activities and family gatherings.
  • Explore outdoor grilling setups that allow you to enjoy barbecues in this inviting area.
  • Relax by a swimming pool or hot tub with views of the natural surroundings common here.

Top Attractions Around Winchester

What attractions are nearby?

While staying in this inviting area, you can enjoy nearby outdoor activities, local events, and cultural experiences that highlight the charm and vibrancy of Winchester, California.

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Family Activities

  • San Bernardino County Museum: Explore engaging exhibits and interactive displays that captivate the whole family, making it a highlight in this region's cultural scene.
  • Cajon Pass: Enjoy scenic drives through the area with breathtaking mountain views, perfect for a family outing in this part of California.
  • Dave & Buster's San Bernardino: Have fun with arcade games and entertainment options designed to entertain children and adults alike in nearby surroundings.
  • The Castle Park Amusement Center: Experience exciting rides and attractions tailored for families seeking adventure and entertainment here in the destination.
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Adult Activities

  • Winchester Community Park: Enjoy outdoor activities like walking, jogging, or picnicking in this expansive local park designed for relaxation and exercise.
  • Hot Air Balloon Rides: Experience breathtaking aerial views of the area’s scenic landscape through guided hot air balloon excursions available nearby.
  • Wine Tasting Tours: Explore the region's renowned wineries to sample exquisite local wines, perfect for a sophisticated day out.
  • Golf Courses: Play a round at premier golf courses in the area that offer picturesque views and challenging fairways for enthusiasts of all skill levels.

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Winchester Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Research local events and nearby attractions to maximize your time and enjoy authentic experiences in the region.
  • Select a Well-Located Rental: Choose a property that offers easy access to key sights and amenities to make your stay more convenient and enjoyable.
  • Explore Local Cuisine: Take advantage of the area’s dining options to experience regional flavors and support local businesses during your visit.
  • Respect the Neighborhood: Adhere to community guidelines and be considerate of neighbors to ensure a peaceful and pleasant stay in this destination.

Transportation Options

  • Personal Vehicle: Renting or using your own car offers the most flexibility for exploring the region and accessing various rental properties here in Winchester.
  • Public Transit: Local bus services provide an affordable and convenient way to navigate the area, connecting you to nearby attractions and amenities within the region.
  • Rideshare Services: Companies like Uber and Lyft operate in this destination, offering a reliable and quick transportation option for traveling around here with ease.
  • Taxi Services: Traditional taxi providers are available in the region, providing comfortable and direct transportation to your rental home and local destinations.

Local Customs Options

  • Western Heritage Celebrations: You can participate in or observe local events that honor the region’s rich history and cowboy traditions, adding a cultural touch to your stay.
  • Farmers’ Market Traditions: Visiting the area’s farmers' markets allows you to experience the community’s agricultural roots and enjoy fresh, locally grown produce.
  • Native American Influences: Respect for indigenous customs and art is prevalent here, offering an authentic glimpse into the area's original inhabitants.
  • Community Festivals: Embrace the lively spirit of local festivals which celebrate regional crafts, music, and cuisine, making your trip more memorable.

Frequently Asked Questions About Winchester Rentals by Owner

1. What are the top vacation rentals in Winchester?

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

2. How many Rentbyowner vacation rentals are available in Winchester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 128 in the Winchester 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 Winchester. 

3. What is the cancellation policy for rental properties in Winchester, California?

The cancellation policy varies depending on the individual owner’s listing. You should review the specific terms outlined in the rental listing or contact the owner directly to understand the refund policy and any applicable fees.

4. How do I ensure the rental by owner in Winchester, California, meets my needs before booking?

You can verify property details, amenities, and house rules listed online. Additionally, reaching out to the owner with questions helps you confirm that the accommodation aligns with your preferences for your stay in this area.

5. Are there any additional fees when booking a rental by owner here?

Additional fees such as cleaning or service charges are often noted in the listing description. It’s important to review these details carefully or inquire directly with the owner to avoid surprises during your reservation process.

6. What should I know about check-in and check-out times for rentals in this region?

Check-in and check-out times are typically specified within the listing. Contact the owner beforehand if you have special scheduling requests or need flexibility during your visit to this destination.

7. Is there a secure payment method available for booking rental properties in Winchester, California?

Reputable rental by owner listings usually offer secure payment options through the booking platform. Always confirm that transactions are protected and communicate only through official channels to ensure a safe transaction.

More Rentals You May Like Near Winchester

More Top-Rated Rentals by Owner in Winchester Area