Best Vacation Homes in Windsor
Cottage
10.0(66 Reviews)
1 Bedroom
1 Bath
5 Guests
649 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
R2,545/Night
7 Nights - R17,814
House
10.0(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
3003.13 ft²
- Oceanfront
Pool- Ocean View
- Balcony/Terrace
R7,403/Night
7 Nights - R51,822
Bed & Breakfast
10.0(73 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
Breakfast
Kitchen
Parking
R2,597/Night
7 Nights - R18,175
House
10.0(61 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R2,397/Night
7 Nights - R16,783
Villa
10.0(2 Reviews)
7 Bedrooms
3 Baths
16 Guests
322.92 ft²
- Fireplace/Heating
View- Parking
Air Conditioner
R14,496/Night
7 Nights - R101,467
House
10.0(60 Reviews)
2 Bedrooms
1 Bath
6 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,165/Night
7 Nights - R36,153
Cottage
10.0(51 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R5,447/Night
7 Nights - R38,134
Cottage
10.0(39 Reviews)
2 Bedrooms
1 Bath
4 Guests
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,939/Night
7 Nights - R55,572
Windsor Luxury Rentals
New
House
2 Bedrooms
1 Bath
6 Guests
1496.18 ft²
- Parking
Internet
Child Friendly
Security/Safety
R54,763/Night
7 Nights - R383,337
House
6 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R20,240/Night
7 Nights - R141,680
New
Condo
6 Bedrooms
6 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R14,826/Night
7 Nights - R103,775
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R13,324/Night
7 Nights - R93,264
House
10.0(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
4000 ft²
Private Pool- Hot Tub
Spa- Fireplace/Heating
R11,199/Night
7 Nights - R78,396
House
8.6(4 Reviews)
4 Bedrooms
3 Baths
10 Guests
6000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
R10,234/Night
7 Nights - R71,634
House
4.0(1 Review)
7 Bedrooms
5 Baths
19 Guests
2723 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R10,221/Night
7 Nights - R71,552
House
9.6(42 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R9,720/Night
7 Nights - R68,048
Windsor Pet Friendly Vacation Rentals
Cottage
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,010/Night
7 Nights - R28,064
New
House
10.0(2 Reviews)
1 Bedroom
2 Baths
5 Guests
13928.5 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,880/Night
7 Nights - R20,156
Cottage
1 Bedroom
1 Bath
Pet Friendly- Kitchen
- Air Conditioner
- Child Friendly
R3,023/Night
7 Nights - R21,155
House
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R2,992/Night
7 Nights - R20,942
Apartment
10.0(1 Review)
1 Bedroom
2 Baths
6 Guests
150.69 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
R2,816/Night
7 Nights - R19,714
Cottage
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,922/Night
7 Nights - R13,459
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,814/Night
7 Nights - R12,706
Cottage
9.8(119 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R3,622/Night
7 Nights - R25,346
Windsor Large Vacation Homes
Cottage
10.0(42 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,330/Night
7 Nights - R37,315
Villa
9.5(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
96.88 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
R1,549/Night
7 Nights - R10,839
House
10.0(29 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,178/Night
7 Nights - R43,242
House
8.8(14 Reviews)
5 Bedrooms
2 Baths
10 Guests
118.4 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
R2,728/Night
7 Nights - R19,092
House
10.0(4 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R4,518/Night
7 Nights - R31,634
House
9.8(24 Reviews)
5 Bedrooms
2 Baths
10 Guests
2200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,941/Night
7 Nights - R20,582
House
9.8(18 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R5,940/Night
7 Nights - R41,589
Cottage
9.8(17 Reviews)
3 Bedrooms
2 Baths
10 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R5,859/Night
7 Nights - R41,016
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.
Best Times to Visit Windsor
When should you plan your Vacation Rentals stay?
Timing your visit to Windsor, Ontario, Canada, can greatly enhance your experience, as the best moments to explore this destination depend on the climate and local events that align with your travel preferences.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for outdoor activities and exploring the area’s vibrant events and festivals. This is when demand for vacation rentals peaks, so booking early ensures a comfortable stay.
Average Temperature Daytime: 25°C - Nighttime: 15°C
Fall (September to October)
Early fall offers mild temperatures and beautiful foliage, attracting visitors seeking scenic drives and outdoor leisure. Vacation rentals are in high demand, especially during this picturesque season in the region.
Average Temperature Daytime: 20°C - Nighttime: 10°C
Off-Season Highlights
Winter (November to February)
The winter months see a quieter atmosphere, with cooler weather inviting cozy getaways and indoor activities. Booking your stay during this time can offer more flexibility and affordable rates for vacation rentals.
Average Temperature Daytime: 0°C - Nighttime: -5°C
Spring (March to May)
In early spring, the area starts to awaken with milder temperatures and blooming landscapes. It’s an ideal off-peak period for those seeking a peaceful retreat, with lesser competition for vacation rentals.
Average Temperature Daytime: 10°C - Nighttime: 3°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
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 spaces where you can savor meals while taking in the fresh air of this region.
- Take advantage of private patios or decks perfect for relaxing or entertaining guests outside.
- Make the most of spacious yards or gardens ideal for outdoor activities and leisurely strolls.
- Utilize outdoor grills available for barbecues, bringing a taste of local cuisine to your stay.
- Benefit from scenic porches or verandas that offer a comfortable spot to unwind and enjoy the surroundings.
- Explore nearby parks or walking trails easily accessible from your rental, perfect for outdoor adventures.
- Relax in inviting outdoor seating areas designed for socializing or enjoying peaceful moments in nature.
Top Attractions Around Windsor
What attractions are nearby?
In this vibrant destination, you can explore a variety of nearby activities, from scenic parks and cultural attractions to local dining experiences, ensuring your stay in Windsor, Ontario, is both enjoyable and memorable.
Family Activities
- Windsor Riverfront Park: Enjoy a family picnic and scenic views along the Detroit River at this popular outdoor destination.
- The Windsor Sculpture Park: Explore contemporary art installations that are perfect for family photos and leisurely strolls in this open-air gallery.
- Caesars Windsor Casino: Experience exciting entertainment options suitable for older children and teens while enjoying the vibrant atmosphere of this renowned casino complex.
- Adventure Bay Family Water Park: Dive into fun with water slides, wave pools, and lazy rivers designed to keep the entire family entertained for hours near here.
Adult Activities
- Wine Tasting Tours: Explore the region's renowned wineries and enjoy guided tastings that showcase the area's rich viticultural heritage.
- Cultural and Historic Sites: Discover the area's fascinating history by visiting local museums and heritage sites that highlight Windsor's unique past.
- Parks and Outdoor Recreation: Relax in the area's beautiful parks, where you can indulge in outdoor activities like walking, picnicking, or simply enjoying nature.
Other Places to Stay in Windsor, ON
South Central
Bridgeview
East Windsor
Sandwich Towne
Tecumseh
Riverside
LaSalle
Leamington
Walkerville
Wheatley
McGregor
Amherstburg
Windsor Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the region’s diverse culinary scene by visiting popular eateries close to your vacation rental for authentic flavors.
- Plan outdoor activities: Make the most of Windsor’s parks and waterfront areas by scheduling outdoor adventures that suit your interests, from walking trails to relaxing by the river.
- Visit nearby attractions: Discover cultural and historical sites in the area to enrich your stay and get a true sense of the destination’s unique heritage.
- Utilize local transportation: Use available transit options or walk when possible to efficiently explore the region and experience its hidden gems firsthand.
Transportation Options
- Windsor Transit Bus Service: This reliable public transportation option allows you to conveniently navigate the area and access key destinations within the city.
- Windsor Express Bus:** An efficient bus service connecting various parts of the region, ideal for exploring beyond your vacation rental.
- Taxi and Rideshare Services: Easily available here, these options offer flexible and quick transportation for any travel needs around the destination.
- Car Rentals: Choosing a rental vehicle gives you the freedom to explore Windsor and nearby attractions at your own pace.
Local Customs Options
- Tea Time Tradition: Engaging in the local tea time customs, you’ll find that sharing a pot of tea is a cherished way to connect with friends and family here in Windsor.
- Festive Celebrations: Participating in regional festivals and parades offers a vibrant glimpse into the area's community spirit and cultural heritage during your stay.
- Local Cuisine Etiquette: Appreciating the region’s culinary traditions involves savoring hearty regional dishes with an emphasis on hospitality and shared meals.
- Respect for Historical Sites: When exploring this destination, you'll notice a strong respect for its historical landmarks, reflecting the community’s pride and preservation efforts.
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:
- 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
- Another Sunset by the Bay: Waterfront - 2-Bedroom
- 'PELEE SHORES' Point Pelee Lakefront Vacation Cottage
- Sandy Beach, Waterfront. Birders, Wineries.
- Sunsets by the Bay - Your Waterfront Oasis
- Spacious Lakefront 4 Bedroom
- Point Pelee Beach Retreat | Hot Tub | Lake Erie
2. How many vacation rentals have private pools in Windsor?
There are 16 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 2026 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.
5. What is the cancellation policy for vacation rentals in Windsor, Ontario?
Cancellation policies vary by listing, so you should review the specific terms on the property page or contact the host directly to understand the terms applicable to your booking.
6. How do I ensure my stay in Windsor vacation rentals is secure and reliable?
Booking through a trusted platform provides secure payment options and verified hosts, offering peace of mind for your stay in this region. Always read reviews and communicate with hosts before confirming your reservation.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning charges, service fees, or local taxes may apply depending on the listing. Check the detailed fee breakdown on the property’s page before completing your reservation.
8. Can I modify or extend my stay at a Windsor vacation rental after booking?
Modifications and extensions depend on the host’s policies and availability. It's recommended to contact the host directly as soon as possible to discuss any changes to your reservation.
9. What amenities are typically available in vacation rentals in Windsor, Ontario?
Most properties offer essential amenities like Wi-Fi, parking, and fully equipped kitchens. To confirm specific amenities, review the property details listed or reach out directly to the host.
Windsor Top Rated Vacation Rentals
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R8,131/Night
7 Nights - R56,914
House
10.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
3500 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R5,623/Night
7 Nights - R39,362
Hotel
9.8(60 Reviews)
1 Bath
- Pool
- Breakfast
- Parking
- Internet
R2,186/Night
7 Nights - R15,309
R2,310/Night
7 Nights - R16,177
Hotel
9.2(1089 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
R1,995/Night
7 Nights - R13,967
Hotel
8.8(1378 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
R2,073/Night
7 Nights - R14,507
Hotel
8.8(1005 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
R1,871/Night
7 Nights - R13,099
Hotel
8.8(140 Reviews)
8 Baths
348.48 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R2,149/Night
7 Nights - R15,047
