Discover Your Perfect Windsor Vacation Homes

Best Vacation Homes in Windsor

Cottage
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2 Bedrooms 2 Baths 6 Guests 1064 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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AU $274/Night 7 Nights - AU $1,920
House
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like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests 516.67 ft²
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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AU $140/Night 7 Nights - AU $980
Apartment
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1 Bedroom 1 Bath 200 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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AU $395/Night 7 Nights - AU $2,764
House
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like-icon10.0
Exceptional
(100 Reviews)
4 Bedrooms 3 Baths 15 Guests 4500 ft²
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    Fireplace/Heating
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    Balcony/Terrace
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AU $527/Night 7 Nights - AU $3,688
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Apartment
1 Bedroom 1 Bath 2 Guests 301.39 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • Breakfast
    Breakfast
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AU $160/Night 7 Nights - AU $1,121
Cottage
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like-icon10.0
Exceptional
(56 Reviews)
2 Bedrooms 1 Bath 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
AU $207/Night 7 Nights - AU $1,451
House
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like-icon10.0
Exceptional
(9 Reviews)
2 Bedrooms 2 Baths 6 Guests 1600 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $702/Night 7 Nights - AU $4,914
House
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like-icon10.0
Exceptional
(8 Reviews)
5 Bedrooms 5 Baths 16 Guests 4000 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $2,079/Night 7 Nights - AU $14,554

Windsor Luxury Rentals

House
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like-icon10.0
Exceptional
(18 Reviews)
19 Bedrooms 19 Baths 50 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
AU $6,061/Night 7 Nights - AU $42,428
House
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like-icon10.0
Exceptional
(5 Reviews)
4 Bedrooms 4 Baths 14 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
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AU $1,138/Night 7 Nights - AU $7,963
House
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like-icon10.0
Exceptional
(7 Reviews)
6 Bedrooms 3 Baths 16 Guests 2896 ft²
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    Fireplace/Heating
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AU $900/Night 7 Nights - AU $6,298
House
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like-icon9.4
Exceptional
(3 Reviews)
3 Bedrooms 2 Baths 10 Guests 2042 ft²
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    Fireplace/Heating
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    Air Conditioner
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AU $505/Night 7 Nights - AU $3,537
Other
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like-icon9.8
Exceptional
(19 Reviews)
2 Bedrooms 2 Baths 6 Guests 2500 ft²
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    Fireplace/Heating
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    Kitchen
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AU $465/Night 7 Nights - AU $3,255
House
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like-icon9.8
Exceptional
(19 Reviews)
3 Bedrooms 2 Baths 8 Guests 3000 ft²
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    Fireplace/Heating
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    Balcony/Terrace
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AU $403/Night 7 Nights - AU $2,825
House
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like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 8 Guests 1512 ft²
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    Fireplace/Heating
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    Balcony/Terrace
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AU $402/Night 7 Nights - AU $2,818
House
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 3 Guests 600 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
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AU $398/Night 7 Nights - AU $2,783

Windsor Pet Friendly Vacation Rentals

Cabin
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $391/Night 7 Nights - AU $2,741
Other
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
1 Bedroom 1 Bath 6 Guests 452.08 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $277/Night 7 Nights - AU $1,938
Cabin
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like-icon9.8
Exceptional
(18 Reviews)
1 Bedroom 1 Bath 4 Guests 40 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $383/Night 7 Nights - AU $2,681
Other
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 204.51 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $216/Night 7 Nights - AU $1,512
Cabin
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like-icon9.6
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $383/Night 7 Nights - AU $2,681
Cabin
Map-icon
like-icon9.4
Exceptional
(9 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $391/Night 7 Nights - AU $2,741
RV Rental
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1 Bedroom 1 Bath 6 Guests
  • Pet Friendly
    Pet Friendly
  • Child Friendly
    Child Friendly
More amenities
AU $104/Night 7 Nights - AU $725
Cabin
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
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AU $282/Night 7 Nights - AU $1,974

Windsor Large Vacation Homes

Villa
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like-icon10.0
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 2 Guests 600 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $326/Night 7 Nights - AU $2,282
Apartment
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1 Bedroom 1 Bath 200 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Kitchen
    Kitchen
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AU $395/Night 7 Nights - AU $2,764
House
Map-icon
like-icon9.4
Exceptional
(15 Reviews)
3 Bedrooms 2 Baths 14 Guests
  • Fireplace/Heating
    Fireplace/Heating
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    Balcony/Terrace
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AU $379/Night 7 Nights - AU $2,654
House
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4 Bedrooms 3 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Air Conditioner
    Air Conditioner
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AU $656/Night 7 Nights - AU $4,589
House
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3 Bedrooms 2 Baths 12 Guests 1800 ft²
  • View
    View
  • Kitchen
    Kitchen
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AU $551/Night 7 Nights - AU $3,856
House
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3 Bedrooms 2 Baths 14 Guests
  • View
    View
  • Kitchen
    Kitchen
More amenities
AU $226/Night 7 Nights - AU $1,585
House
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3 Bedrooms 2 Baths 10 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
AU $354/Night 7 Nights - AU $2,480
New
House
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5 Bedrooms 4 Baths 16 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $1,126/Night 7 Nights - AU $7,879

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 optimal time to visit this destination can enhance your experience, allowing you to enjoy the region's climate and local events while ensuring your stay in Windsor, McGregor is truly memorable.

Peak Season Highlights

spring
Spring (March to May)

During spring, you can enjoy pleasant weather and blooming landscapes, making it a popular time to visit the area for outdoor activities and sightseeing.

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

Fall offers cooler temperatures and vibrant foliage, ideal for exploring the region’s scenic beauty and enjoying outdoor leisure activities.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Summer (June to August)

In summer, the area experiences hotter temperatures, which is perfect if you prefer warm weather for outdoor adventures or relaxing by the water.

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

Winter tends to be cooler and quieter, offering a tranquil escape with fewer visitors and lower accommodation rates.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windsor

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 outdoor dining areas perfect for meals with a view of the scenic surroundings.
  • Make use of spacious patios or decks for relaxing and entertaining outdoors.
  • Take advantage of private pools or hot tubs to unwind after exploring the region.
  • Benefit from well-maintained gardens or landscaped yards ideal for outdoor activities.
  • Utilize outdoor grills or barbecue stations for family cookouts in the fresh air.
  • Experience the convenience of outdoor fire pits for cozy evenings under the stars.
  • Explore nearby walking trails or nature paths directly accessible from your rental.
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Family Activities

  • Windsor Park: Enjoy a family picnic and outdoor activities at this scenic park nestled in the heart of this charming area.
  • McGregor Historic District: Explore the rich history and charming architecture that offers an educational experience for visitors of all ages.
  • Local Farmers Market: Discover fresh local produce and handcrafted goods, making it a fun outing for families looking to support regional farmers and artisans.
  • Community Events and Festivals: Participate in seasonal events that bring families together for entertainment, music, and local culture within the region.
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Adult Activities

  • Wine Tasting at local vineyards: Experience the region's renowned wineries by sampling exquisite Texas wines amid picturesque vineyard settings.
  • Golfing at championship courses: Enjoy a day on meticulously maintained golf courses that cater to all skill levels, offering scenic views and challenging play.
  • Visit historical sites and museums: Discover the area's rich history through well-preserved landmarks and engaging exhibits that appeal to culture enthusiasts.
  • Enjoy outdoor recreational activities: Engage in activities like fishing, hiking, or kayaking in nearby lakes and parks that showcase the natural beauty of this destination.

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take time to discover the area's charming spots and outdoor activities to truly immerse yourself in the local vibe.
  • Plan Ahead for Dining: Research nearby restaurants or cafes to enjoy authentic regional cuisine during your stay here.
  • Utilize Transportation Options: Make use of available transportation services or consider renting a vehicle to navigate the region conveniently.
  • Check Seasonal Events: Look into local events and festivals happening during your visit to enhance your experience in this destination.

Transportation Options

  • Personal Vehicle: Renting or using your own car offers the most flexibility for exploring the area and reaching your vacation rental in Windsor, McGregor, Texas.
  • Local Taxi Services: Reliable taxi services are available for convenient transfers to and from your stay within this region, ensuring a stress-free travel experience.
  • Ridesharing Options: Rideshare apps provide an easy way to navigate around here, giving you affordable and quick transportation directly to your vacation rental.
  • Public Transit: Although limited, regional bus services can connect you to key spots in the area, making it a practical option for budget-conscious travelers.

Local Customs Options

  • Southern Hospitality: You’ll find that locals in this region take pride in welcoming visitors with friendly manners and warm greetings, reflecting the area's heartfelt hospitality.
  • Engaging with local agricultural customs, you might observe or participate in traditional livestock activities that have been part of the area's heritage for generations.
  • Local Festivals: Participating in community-driven festivals here provides a glimpse into longstanding traditions rooted in regional history and culture.
  • Religious Observances: Respect for local religious practices often plays an important role, with community events and gatherings centered around faith-based customs.

Frequently Asked Questions About 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 2026 is over 67 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 a vacation rental in Windsor, McGregor?

The cancellation policy varies depending on the specific property you choose. It’s recommended to review the listing details or contact the owner directly to understand their terms regarding cancellations and refunds.

5. How do I book a vacation rental in Windsor, McGregor?

Booking is straightforward through the property’s listing page. You can select your dates, review the amenities, and proceed with the reservation online. For any questions, reaching out to the property owner can help clarify booking details.

6. Are there any additional fees associated with staying in a holiday home in this area?

Additional fees such as cleaning fees, service charges, or security deposits may apply depending on the property. These details are typically outlined in the listing, so be sure to review them before finalizing your booking.

7. What amenities can I expect in a vacation rental in the region?

Most properties offer essential amenities to ensure a comfortable stay, including Wi-Fi, fully equipped kitchens, and outdoor spaces. Specific amenities are listed on each property page, so check the details of your preferred rental.

8. Is it possible to communicate directly with the property owner in Windsor, McGregor?

Yes, direct communication with the owner is encouraged to ask questions about the property, confirm availability, or discuss special requests. Contact information is usually provided on the listing, allowing a seamless planning process.

Windsor Top Rated Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(7 Reviews)
1 Bedroom 1 Bath 4 Guests 600 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
AU $354/Night 7 Nights - AU $2,475
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
More amenities
AU $315/Night 7 Nights - AU $2,202
House
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1 Bedroom 1 Bath 2 Guests 600 ft²
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $381/Night 7 Nights - AU $2,670
House
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1 Bedroom 1 Bath 1 Guest
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
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AU $374/Night 7 Nights - AU $2,620
Hotel
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1 Bath
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $317/Night 7 Nights - AU $2,221
House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 8 Guests
  • Private Pool
    Private Pool
  • Hot Tub
    Hot Tub
More amenities
AU $773/Night 7 Nights - AU $5,415
House
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1 Bedroom 1 Bath 2 Guests
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
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AU $321/Night 7 Nights - AU $2,249