Discover Your Perfect Windsor Vacation Homes

Windsor Large Vacation Homes

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8.6 (106 Reviews)
Bed & Breakfast
Lovett Lodge
  • Parking
  • TV
  • Wheelchair Accessible
View Availability
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8.5 (489 Reviews)
Bed & Breakfast
Living on Dee
  • Parking
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
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9.1 (17 Reviews)
Apartment
388 Tay Motel
  • Parking
  • Security/Safety
  • Guest Services
View Availability
See More Family Vacation Rentals in Windsor on FVR

Why Choose Rent By Owner for your Windsor 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 Windsor

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as seasonal variations in Windsor, Southland, New Zealand, influence weather and local activities, making it essential to plan your stay accordingly for a truly memorable getaway.

Peak Season Highlights

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Summer (December to February)

During the summer months, this destination experiences warm weather ideal for outdoor activities and exploration, making it a popular time to stay in the region's vacation rentals.

Average Temperature Daytime: around 20-25°C - Nighttime: around 12-15°C
autumn
Autumn (March to May)

Autumn brings mild temperatures and beautiful foliage, attracting visitors seeking a peaceful retreat and comfortable conditions for outdoor pursuits.

Average Temperature Daytime: around 15-20°C - Nighttime: around 8-12°C

Off-Season Highlights

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Winter (June to August)

In winter, the area offers cooler temperatures and fewer tourists, providing a quieter experience whether you're seeking relaxation or indoor attractions in the region.

Average Temperature Daytime: around 8-12°C - Nighttime: around 2-5°C
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Spring (September to November)

Spring features transitional weather with blooming nature, making it an ideal time for travelers looking to avoid crowds while enjoying pleasant days in the region.

Average Temperature Daytime: around 12-17°C - Nighttime: around 5-9°C

Weekly Weather Forecast for Windsor

How to Book Your Windsor 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 Windsor

More Top-Rated Vacation Rentals in Windsor 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 private outdoor seating areas perfect for relaxing and entertaining amidst the scenic surroundings.
  • Benefit from spacious gardens or lawns ideal for outdoor activities and family gatherings in the region's peaceful environment.
  • Make use of barbecue grills to enhance your outdoor dining experience, taking advantage of the favorable climate here.
  • Experience outdoor fire pits or fireplaces that create cozy evenings under the stars in this picturesque destination.
  • Take advantage of designated outdoor dining spaces to savor meals alfresco while soaking in the natural beauty nearby.
  • Explore the landscaped yards or walking paths that encourage outdoor exploration and leisure in the area.
  • Utilize available outdoor storage for equipment such as bikes or kayaks, supporting active adventures here in the region.

Top Attractions Around Windsor

What attractions are nearby?

In this charming area of Southland, you can enjoy a variety of outdoor activities such as exploring scenic walking trails, fishing in pristine waters, or experiencing local wildlife, all conveniently accessible from your vacation rental nearby.

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Family Activities

  • Windsor Forest Walk: Embark on a scenic family stroll through the lush greenery of Windsor Forest, perfect for picnics and outdoor adventures in the region.
  • Southland Museum and Art Gallery: Explore engaging exhibits and interactive displays that captivate children and adults alike, offering a cultural experience in this destination’s nearby town center.
  • Local Wildlife Parks: Visit nearby wildlife parks where your family can observe native animals and learn about conservation efforts in the area.
  • Community Events and Festivals: Participate in seasonal festivals or outdoor markets held throughout the year, providing fun and entertainment for every family member here in the region.
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Adult Activities

  • Windsor Golf Course: Enjoy a relaxing day on the greens at this scenic golf course, perfect for both beginners and seasoned players looking to unwind in the region.
  • Southland Museum and Art Gallery: Discover regional history and contemporary art exhibitions that offer cultural insights into this part of New Zealand's Southland.
  • Walking Trails in the Area: Explore local walking trails that showcase the area's natural beauty, making it an excellent activity for outdoor enthusiasts staying nearby.
  • Local Wineries and Tastings: Visit nearby wineries for tastings and tours, offering a taste of the region’s renowned wines while enjoying the picturesque landscape.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for the Region's Weather: Check the local forecast before your trip to make the most of outdoor activities in this scenic area.
  • Explore Local Cuisine and Markets: Take time to enjoy the regional flavors by visiting nearby markets and eateries to experience authentic tastes.
  • Utilize Nearby Recreation Opportunities: Maximize your stay by exploring nearby parks, trails, or waterways that showcase the area's natural beauty.
  • Choose Well-Located Vacation Rentals: Select accommodations close to key attractions and amenities to simplify your travel plans and enhance convenience.

Transportation Options

  • Windsor, Southland Bus Services: Accessible local bus routes connect you to key points within the region, offering a convenient way to explore here without a car.
  • Rental Cars: Car rental options in the area provide flexibility and independence to discover the surrounding attractions at your own pace.
  • Private Transfers: Private transportation services are available for a comfortable and direct journey to and from Windsor’s vacation rentals.
  • Cycling and Walking Paths: Well-maintained trails allow you to enjoy the scenic beauty of this destination on foot or by bike, making it easy to access nearby amenities and natural sights.

Local Customs Options

  • Welcoming Hospitality: Locals pride themselves on their friendly and warm attitude, making visitors feel at home in this charming part of Southland.
  • Traditional Gatherings: Community events often feature hearty local foods and music, reflecting the region’s close-knit and convivial spirit.
  • Respect for Nature: You’ll notice a deep appreciation for the natural environment, with customs that emphasize conservation and outdoor enjoyment.
  • Indigenous Heritage: The area honors its Māori roots through respectful recognition of cultural practices and stories shared during local festivities.

Frequently Asked Questions About Windsor?

1. What are the top vacation rentals in Windsor?

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

2. Which vacation homes in Windsor are best for families?

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

3. How many Rentbyowner vacation rentals are available in Windsor?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 139 in the Windsor 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 Windsor. 

4. What is the cancellation policy for vacation rentals in Windsor, Southland?

Cancellation policies vary by listing. You should review the specific rental's cancellation terms on its page or contact the property owner directly to understand the conditions, including any potential fees or deadlines.

5. How do I confirm availability and secure my booking at a holiday home in this region?

Availability can be checked directly on the listing. Once you find your preferred dates, you can proceed with the booking through the platform or contact the owner for assistance to ensure your reservation is confirmed.

6. Are there any specific house rules or requirements for staying at a rental here?

Each property sets its own house rules, which are detailed in the listing. It’s important to read these carefully before booking and to communicate with the host if you have any questions.

7. What amenities can I expect when staying at a vacation rental in this area?

Amenities vary depending on the property, but common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Check the listing description for a comprehensive list of what’s included.

8. Is there support available if I encounter issues during my stay in the region?

Support is typically provided by the property owner or local management team. Contact details are provided in the listing, and you can reach out for assistance during your stay to ensure a smooth experience.