Best Vacation Homes in Windsor
Cottage
- Air Conditioner
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- TV
Apartment
- Air Conditioner
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- Pet Friendly
Cottage
- Air Conditioner
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- TV
House
- Air Conditioner
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- Pet Friendly
Windsor Luxury Rentals
Villa
- Air Conditioner
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- Air Conditioner
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- Pool
House
- Air Conditioner
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- Pool
House
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- Security/Safety
Windsor Pet Friendly Vacation Rentals
Cottage
- Air Conditioner
- Parking
- Pet Friendly
Apartment
- Air Conditioner
- Pet Friendly
- Security/Safety
House
- 118 ft² House
- Air Conditioner
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- Pet Friendly
Apartment
- Air Conditioner
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- Pet Friendly
House
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- Pet Friendly
Apartment
- Air Conditioner
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- Pet Friendly
Cottage
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- Pet Friendly
Windsor Large Vacation Homes
House
- Air Conditioner
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House
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House
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- TV
Why Choose Rent By Owner for your Windsor Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
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
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
Other Places to Stay in Windsor, ON
Windsor Vacation Rental Frequently Asked Questions
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:
- Wenzler's Landing Bed & Breakfast
- Beach House with Stunning Lake Views & Beautiful Sunsets- 3 Bedrooms, 2 Baths
- Omstead's On Erie
- Bird's Nest at Hillman Marsh - Cute cozy cottage - WIFI now available!
- Bunker by the Bay - Perfect Couples Getaway
- 'PELEE SHORES' Point Pelee Lakefront Vacation Cottage
- Another Sunset by the Bay: Waterfront - 2-Bedroom
- CJs Lakehouse is 1km to Point Pelee. Huge yard, firepit, pets welcome!
- Sunsets by the Bay - Your Waterfront Oasis
- Sandy Beach, Waterfront. Birders, Wineries.
2. How many vacation rentals have private pools in Windsor?
There are 13 vacation rentals with private pools near Windsor. Top-rated RBO homes that have access to a swimming pool include:
3. 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:
4. How many Rentbyowner vacation rentals are available in Windsor?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 641 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.
