Windsor vacation rentals

We found 310 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Windsor by choosing from 93 houses, 90 apartments, and other vacation rentals. Whether you’re staying in a vacation home with friends, family, or even just your pets, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

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Find out more about Windsor

Why visit Windsor

  • Picturesque Riverfront: Stroll along the scenic Windsor Riverfront, perfect for relaxing walks and stunning views.
  • Family-Friendly Activities: Enjoy a variety of attractions suitable for all ages, ensuring fun for the entire family.
  • Charming Neighborhoods: Explore East Windsor's friendly neighborhoods that offer a warm and welcoming atmosphere.
  • Diverse Accommodation Options: Choose from cozy cottages to spacious homes, catering to every traveler's budget.
  • Vibrant Local Culture: Experience the lively atmosphere filled with friendly locals and engaging urban experiences.

Popular types of accommodation in Windsor

If you're looking for the perfect getaway in Windsor, you're in the right place. Our selection of vacation rentals includes charming cottages, spacious houses, and comfortable apartments. Whether you're seeking a cozy cottage or a larger house rental, Windsor has something to suit every traveler's needs. Enjoy transparency and savings as you explore our top-notch vacation homes in this beautiful destination.

  • Cottages: The top choice for vacation rentals in Windsor, offering a cozy and charming escape surrounded by nature.
  • Houses: A popular option for families and groups, these homes provide spacious amenities and a home-like atmosphere.
  • Apartments: Ideal for solo travelers or couples, these rentals offer convenient access to local attractions and a comfortable stay.
  • Bed And Breakfast: A delightful way to experience local hospitality, featuring cozy rooms and homemade breakfasts.**

Top attractions in Windsor

Windsor, Ontario, is the perfect destination for romantic getaways, family vacations, or urban adventures. With a wide array of attractions, including vibrant streets, urban parks, and entertainment arenas, there's something for everyone. Whether you're looking for family-friendly activities, outdoor experiences, or a taste of city life, Windsor offers a variety of points of interest that promise to make your visit unforgettable.

  • Detroit Windsor Tunnel: Experience the bustling atmosphere of this unique street connecting Detroit and Windsor. The tunnel offers a fascinating glimpse into the underground passage that plays a crucial role in cross-border travel.
  • Ambassador Bridge: Explore this iconic historic bridge that symbolizes the strong cultural ties between Canada and the U.S. The stunning views of the Detroit skyline and the river make it a must-see.
  • University of Windsor: Walk through the beautiful campus of this historic university, known for its vibrant cultural scene and educational excellence. Enjoy the architecture and local art while soaking in the academic atmosphere.

Things to do recommended for couples

For a romantic getaway in Windsor, explore the enchanting Sanson Estate Winery, only 14 miles away, or indulge in the charm of Muscedere Vineyards, 17 miles from the city. Don't miss the delightful Colio Estate Winery, located 20 miles away, offering a perfect blend of romance and entertainment.

Things to do recommended for families

Families visiting Windsor can have a splash at Adventure Bay Family Water Park, where water slides and wave pools offer fun for everyone. This vibrant waterpark ensures an exciting day filled with laughter and adventure, perfect for creating lasting memories together.

Things to do recommended for groups

In Windsor, your group can shop at Devonshire Mall for a vibrant experience, enjoy the outdoors at Ambassador Golf Club, or relax with a craft beer at Walkerville Brewery for a touch of romance and entertainment. Each spot offers a unique vibe for group travelers.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Windsor

If you're traveling with a group, with family, bringing pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many others on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many families, a getaway wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're searching for vacation rentals that offer special rates for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Windsor

Windsor, Ontario, offers a delightful mix of urban charm and scenic beauty, making it perfect for romantic getaways, family vacations, or city explorations. Stroll along the picturesque Windsor Riverfront, discover East Windsor's friendly neighborhoods, and find cozy vacation homes that cater to every budget. Experience the vibrant atmosphere filled with welcoming locals and family-friendly activities, ensuring a memorable stay in this charming Canadian city.

  • City Centre: City Centre is the bustling heart of Windsor, offering a vibrant urban experience. This neighborhood is perfect for travelers looking for a romantic getaway or a family adventure. Enjoy a variety of attractions, including a water park, theater performances, and educational venues. Key landmarks nearby include a sports facility stadium and event conference venues, making it a hub for entertainment and gatherings. Stroll through the lively streets, dine in local restaurants, and explore the array of shops that define this dynamic area.
  • Walkerville: Known for its charming atmosphere, Walkerville is a delightful neighborhood that captures the essence of Windsor. This area is ideal for those seeking a romantic escape or a fun family outing. Enjoy outdoor activities such as hiking trails and water park visits, or simply relax in the picturesque surroundings. Walkerville is home to notable landmarks, including sports facility stadiums and event venues, ensuring there’s always something happening. The blend of historic architecture and modern amenities makes this neighborhood a unique place to explore.
  • Bridgeview: Bridgeview is a welcoming neighborhood that combines family-friendly activities with romantic charm. With a focus on education and entertainment, visitors can enjoy theater shows and exciting water park experiences. The area is close to key attractions such as sports facility stadiums and event venues, providing ample options for lively outings. Whether you're looking to spend quality time with family or enjoy a night out, Bridgeview offers a diverse range of experiences amidst its friendly community vibe.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostly CloudyLowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyLowSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyAverageSlightly Low
April46.8°F (8.2°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June68.9°F (20.5°C)Light RainMostly SunnyHighSlightly High
July74.1°F (23.4°C)Light RainMostly SunnyHighSlightly High
August72.9°F (22.7°C)Light RainMostly SunnyHighSlightly High
September66.6°F (19.2°C)Light RainMostly SunnyAverageAverage
October54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
November41.9°F (5.5°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can lead to better prices, as they often fluctuate. Additionally, consider booking a longer stay, as this can lead to substantial savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its perks. Become a member of our One Key rewards program to enjoy exclusive savings and earn OneKeyCash on qualifying stays. Sign up today and start reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels, pick up right where you left off, or organize your travel plans. You can easily find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the riverside landscape of Windsor

Enjoy the live music and other features of Windsor. Well-liked for its casino gaming, riverfront and gardens, this city is both cosmopolitan and scenic. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in Windsor

Do you want to discover attractions to visit in the city? Venture out of your cozy vacation rental and experience everything that Windsor has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Adventure Bay Family Water Park (0.4 mi / 0.7 km)
  • Olde Walkerville Neighborhood (1.4 mi / 2.3 km)
  • Belle Isle Aquarium (3 mi / 4.9 km)
  • Ambassador Golf Club (4.7 mi / 7.6 km)
  • Detroit Golf Club (9 mi / 14.4 km)
  • Detroit Zoo (12.8 mi / 20.6 km)

Exploring the natural landscape of Windsor

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your vacation in Windsor. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Windsor Riverfront (0.5 mi / 0.8 km)
  • Detroit Riverwalk (1 mi / 1.7 km)
  • Campus Martius Park (1.3 mi / 2 km)
  • Anna Scripps Whitcomb Conservatory (3 mi / 4.8 km)
  • Coventry Gardens (3.6 mi / 5.8 km)
  • Belle Isle Beach (3.7 mi / 5.9 km)

Transportation options to and around Windsor

The nearest airport is in Windsor, ON (YQG), located 4.8 mi (7.7 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Detroit, MI (DET-Coleman A. Young Municipal), which is 6.7 mi (10.8 km) away.

If you'd rather travel by train, the main station is Windsor Station.

Frequently asked questions

What is the best area to stay in Windsor, Ontario, Canada when booking a vacation rental?
When considering the best area to stay in Windsor, Ontario for a vacation rental, the downtown district is an excellent choice. This vibrant neighborhood offers a mix of culture, entertainment, and dining options, making it a hub for visitors. You can easily access top attractions like the scenic waterfront along the Detroit River, where you can enjoy leisurely walks and stunning views of the skyline across the river. Additionally, the nearby Art Gallery of Windsor showcases a diverse range of artwork and often hosts engaging exhibitions.

Another fantastic area to consider is the historic Walkerville neighborhood. Known for its charming architecture and rich history, this area features unique shops and local breweries, superb for those looking to explore local flavors. The nearby Willistead Manor, a beautiful heritage home with lush gardens, provides a picturesque setting for a relaxing afternoon.

In both these neighborhoods, there is a wide array of vacation rental options available, suiting various preferences and budgets.
How much does it cost to rent a vacation home in Windsor?
Prices for vacation rentals in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Windsor vacation house rentals?
You can find great discounts on house rentals in Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Windsor?
For renting a beach house in Windsor, travelers should consider the waterfront areas along the Detroit River, particularly near the scenic Peche Island and the waterfront parks. The stretch along the river provides a variety of vacation rentals with beautiful views of the water and the Detroit skyline. Many properties in this area often feature amenities such as private balconies, outdoor seating areas, and open-concept living spaces, ideal for enjoying the summer sun and the riverside atmosphere.

In addition, the nearby Sandpoint Beach offers a more relaxed environment, surrounded by green spaces and picnic areas. Rentals here can include charming cottages or modern homes, often equipped with barbecues, fire pits, and easy access to the beach, making it great for families or groups looking to enjoy a beachside retreat.

Furthermore, the Windsor Sculpture Park along the riverfront is a cultural highlight, where visitors can enjoy outdoor art installations while taking leisurely walks or bike rides. Many accommodations in this vicinity provide easy access to both the beach and local attractions, with some properties featuring amenities like bikes or kayaks for rent, allowing guests to explore the area more actively.
What is the most popular type of vacation rental accomodation in Windsor?
In Windsor, apartments are the most popular type of vacation rental, with about 75 available throughout the city. These apartments are typically located in vibrant neighborhoods, providing easy access to local attractions and amenities. Travelers can expect features like fully equipped kitchens, cozy living areas, and often private balconies for enjoying views of the Detroit River or the city skyline.

In addition to apartments, there are around 69 vacation houses available, which cater to families or larger groups seeking more space. These homes generally provide multiple bedrooms, private backyards, and BBQ areas, making them ideal for gatherings and outdoor relaxation. Several condos and cottages are also available, offering alternative accommodation options that retain the comforts of home.
Are there any family house rentals in Windsor?
In Windsor, Ontario, there are numerous family-friendly house rentals available, with around 52 options scattered throughout the city. Neighborhoods like South Windsor and East Windsor offer spacious homes suited for families, featuring amenities such as full kitchens, ample living areas, and often outdoor spaces for children to play. Many of these properties come equipped with conveniences like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for all guests.

Visitors can explore nearby attractions, including the beautiful parks along the waterfront, such as Jackson Park, known for its stunning gardens and playgrounds. Additionally, families can enjoy activities at the Windsor Family Aquatic Centre, superb for a fun day out.
Can I rent a vacation home with a pool or hot tub in Windsor?
In Windsor, Ontario, there are several vacation homes available for rent that feature pools and hot tubs. The city offers a mix of residential neighborhoods where travelers can find these amenities, providing a relaxing retreat during their stay. Many of the rentals come equipped with private pools, inviting hot tubs, and spacious outdoor areas great for gatherings. Inside, guests can expect fully equipped kitchens, comfortable living spaces, and modern conveniences to enhance their stay.
Can I find long-stay vacation rentals in Windsor?
A long-stay vacation rental in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Windsor?
In Windsor, Ontario, there are several pet-friendly house rentals available, providing a variety of options for travelers with pets. Many of these rentals are equipped with modern amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces like patios or gardens, ideal for both relaxation and entertaining.

The city offers easy access to several parks, where pet owners can enjoy leisurely walks and outdoor activities with their furry companions. Notable parks include Ojibway Park, known for its scenic trails and natural beauty, and Jackson Park, which features expansive green spaces and beautiful gardens. These parks provide excellent opportunities for pets to explore and socialize.
Are there any remote work vacation rentals in Windsor?
In Windsor, Ontario, there are numerous vacation rentals well-suited for remote work, with around 127 options available. Travelers can expect properties that cater specifically to remote work needs, featuring amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable desks within the accommodations. The city offers a mix of modern apartments and cozy homes, many of which include additional comforts like fully equipped kitchens, spacious living areas, and sometimes outdoor spaces for relaxation during breaks.

Windsor's neighborhoods, particularly those near the waterfront and downtown, provide convenient access to local cafes and parks, ideal for a change of scenery during work hours. Additionally, travelers can take advantage of the city's cultural offerings, such as museums and galleries, which are just a short distance away. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Windsor vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Windsor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Windsor?
In Windsor, popular vacation rental amenities cater to various traveler needs, making for a comfortable stay. Many rentals include fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining in. Onsite parking is a common feature, providing convenience for those traveling by car. Additionally, many properties come with a coffee and tea maker, ensuring that guests can enjoy a warm beverage at their leisure. For those needing to work or study during their trip, a desk is often included in the accommodations. Moreover, pet-friendly options are available, permitting travelers to bring their furry companions along for the journey.
When is the best time to visit Windsor for a vacation rental?
The best time to visit Windsor for a vacation rental is during the peak season from February to April, when the city comes alive with vibrant activities and events. This period is particularly appealing for travelers seeking a mix of cultural experiences and outdoor adventures. With comfortable temperatures ranging from the low 30s to mid-50s Fahrenheit, visitors can enjoy pleasant weather while exploring Windsor's beautiful parks, gardens, and the scenic waterfront along the Detroit River.

July is another popular month to consider, especially for those who enjoy warm summer days filled with outdoor festivals and events. The atmosphere is lively, making it an ideal time to engage with fellow travelers and partake in local activities, such as exploring the diverse dining scene or visiting the renowned Windsor Sculpture Park.

For those looking for more budget-friendly options, October offers a fantastic opportunity to enjoy a quieter experience. The fall foliage adds a stunning backdrop to your visit, and you can take leisurely strolls through the city's parks or enjoy the local art scene without the hustle and bustle of peak tourist crowds.

Ultimately, whether you prefer the energetic vibe of peak season or the serene beauty of fall, Windsor has something for every traveler.
How early should I book a Windsor vacation rental?
Book your Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Windsor, Ontario, Canada?
In Windsor, Ontario, visitors can explore a variety of attractions that highlight the city's cultural and natural beauty. The waterfront along the Detroit River is a focal point, featuring the scenic Windsor Sculpture Park, which showcases numerous artworks in an outdoor setting. The nearby Dieppe Gardens offers lush green spaces and beautiful views of the river, making it a great spot for relaxation and picnics.

The historic Walkerville neighborhood is another highlight, known for its charming streets and vibrant arts scene. Here, travelers can discover local breweries, unique shops, and the impressive Willistead Manor, a beautiful heritage home surrounded by picturesque gardens.

For those interested in history, the Canadian Club Brand Centre provides insights into the history of Canadian whiskey, while the Windsor Museum offers a glimpse into the region's past through engaging exhibits.
Can I change or cancel my Windsor home rental booking on Vrbo?
To find Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Windsor vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.