Windsor holiday rentals

We found 340 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Windsor by choosing from 108 houses, 90 apartments and other holiday rentals. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a pool. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Windsor

Showing deals for:11 Dec - 18 Dec

Property grounds
Exterior detail
Living area
Interior
Exceptional
(14 reviews)

Prepare to fall in love with this adorably tropical beach front property!

Kingsville

12% off
AU$4,056
for 7 nights, 1 cottage
AU$579 per night
includes taxes & fees
Prepare to fall in love with this adorably tropical beach front property!
Living area
Terrace/patio
Kitchen
Main Bedroom King
Wonderful
(33 reviews)

Waterfront House next to Golf Course.

Lakeshore

7% off
AU$1,782
for 7 nights, 1 home
AU$255 per night
includes taxes & fees
Waterfront House next to Golf Course.
Interior
Room
Interior
Private kitchen
Exceptional
(9 reviews)

DREAM CATCHER INN

Tecumseh

8% off
AU$1,130
for 7 nights, 1 apartment
AU$161 per night
includes taxes & fees
DREAM CATCHER INN
Bright and airy bedroom with comfy queen-size bed and black-out curtains.
Living area
Living area
Property grounds
Exceptional
(20 reviews)

Perfect hideaway with a hot tub and a fireplace

Windsor

12% off
AU$1,719
for 7 nights, 1 home
AU$246 per night
includes taxes & fees
Perfect hideaway with a hot tub and a fireplace
Dining
Living area
Interior
Living area
Wonderful
(11 reviews)

Bright & Luxurious Home with Office Space

Amherstburg

8% off
AU$2,050
for 7 nights, 1 home
AU$293 per night
includes taxes & fees
Bright & Luxurious Home with Office Space
Interior
Living Room / Lounge
We welcome each guest with a local amenity. i.e. Baked Goods, Bevies, Fruits
Workspace or Dining area. Closet Window A/C unit
Exceptional
(19 reviews)

Business Traveller/Couples 1-BED DOWNTOWN KINGSVILLE ~ A Cozy Private Apt SUITE

Kingsville

8% off
AU$1,387
for 7 nights, 1 apartment
AU$198 per night
includes taxes & fees
Business Traveller/Couples 1-BED DOWNTOWN KINGSVILLE ~ A Cozy Private Apt SUITE
Room
Private kitchen
Outdoor dining
Interior
Exceptional
(5 reviews)

3 bedroom LaSalle home bordering Amherstburg & minutes away from Windsor

LaSalle

8% off
AU$1,382
for 7 nights, 1 home
AU$197 per night
includes taxes & fees
3 bedroom LaSalle home bordering Amherstburg & minutes away from Windsor

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Why visit Windsor

  • Scenic Waterfront: Enjoy picturesque views along Windsor's riverfront, perfect for leisurely strolls and picnics.
  • Cultural Attractions: Explore the city's rich history through its diverse museums and galleries showcasing local art and heritage.
  • Urban Parks: Relax in Windsor's vibrant parks, ideal for family outings or romantic walks amid nature.
  • Historic Bridges: Marvel at the architectural beauty of Windsor's bridges, which offer stunning views and photo opportunities.
  • Diverse Neighbourhoods: Discover the unique charm of Windsor's various neighbourhoods, each with its own distinct character and experiences.

Popular types of accommodation in Windsor

Discover Windsor, Ontario, a vibrant city offering diverse holiday rentals from cosy cottages to private holiday homes and apartments, including charming two-bedroom options in downtown Windsor. Enjoy local attractions, scenic riverfront walks, and cultural landmarks. Whether you’re seeking a bedroom apartment in the heart of the city or a peaceful retreat, Windsor promises a memorable stay with its transparent, customer-centric approach to holiday rentals.

  • Cottages: Experience the charm of cosy cottages in Windsor, a top choice for a quaint and relaxing getaway.
  • Private Holiday Homes: Enjoy the privacy and comfort of entire homes, providing a home-away-from-home experience in Windsor.
  • Apartments: Opt for stylish apartments in Windsor, ideal for those who appreciate modern conveniences during their stay.
  • Bed And Breakfast: Relish the warm, welcoming ambience of bed and breakfast accommodations for a delightful break in Windsor.**

Top attractions in Windsor

Windsor, Ontario offers a delightful mix of urban charm and rich history, perfect for a romantic or family getaway. Wander along its scenic streets, explore its vibrant urban parks, and marvel at its historic bridges. This dynamic city provides a blend of cultural attractions and outdoor delights, ensuring a memorable experience for every traveller seeking both city sophistication and family-friendly adventures.

  • Ambassador Bridge: A historic bridge in Windsor offering captivating cultural vibes and scenic views over the river.
  • Olde Walkerville Neighborhood: A vibrant town neighbourhood characterised by city vibes, with heritage architecture and lively local haunts.
  • Detroit Windsor Tunnel: A notable street in Windsor that epitomises urban energy, providing a glimpse into the city’s bustling life.

Things to do recommended for couples

Windsor offers a charming getaway for couples. Stroll hand-in-hand along the picturesque waterfront, explore the enchanting gardens of the Windsor Sculpture Park, or indulge in a romantic dinner at a local bistro. Don't forget to take a sunset cruise on the Detroit River for a truly memorable experience.

Things to do recommended for families

Families visiting Windsor can have a delightful day at the Canadian Historical Aircraft Association, where kids can explore fascinating aircraft. Take a stroll along the scenic waterfront, and don't miss the Adventure Bay Family Water Park for some splashing fun.

Things to do recommended for groups

Experience the thrill of motorsport at the Essex County ATV Club Trails, both East and West, located 23km and 19km from Windsor respectively. Enjoy the adrenaline rush and adventure vibes as you navigate these exciting trails with your group.

*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

Whether you're travelling with a group, as a family, with your pets, or planning an extended stay, be sure to apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Windsor with a group: Consider how many bedrooms you'll require, along with features like a fully-equipped kitchen or an outdoor area for a group get-together. Luckily, you can refine your search to include all these, and more, on Stayz.
  • Traveling to Windsor with young kids: Traveling with young children can be challenging. You must prioritise their comfort and safety, ensuring the availability of child-friendly amenities such as a private swimming pool. Additionally, it's advisable to consider the property's proximity to attractions suitable for families.
  • Taking your pets with you to Windsor: For some, a family holiday is incomplete without the presence of their furry companion. If this resonates with you, explore Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Windsor: If you’re seeking holiday lets with offers for extended stays of a month or more, you’ve come to the right place. By utilising the appropriate filter, you can effortlessly locate and secure savings on monthly rentals. Consider including features such as a parking space, a well-equipped kitchen or a private pool in your search criteria, too.

Where to stay in Windsor

Windsor offers a delightful blend of urban vibrancy and scenic charm. Explore downtown Windsor's lively streets, enjoy the relaxed ambience of south Windsor, and savour the waterfront views in western Windsor. Ideal for romantic, family, or city-themed holidays, Windsor provides a rich cultural tapestry and a variety of neighbourhood experiences, ensuring a memorable stay for every traveller.

  • City Centre: Nestled within Windsor’s vibrant core, City Centre offers a blend of romantic, city-themed and family experiences set against an urban backdrop. Visitors can enjoy a variety of attractions including a water park, theatre, and educational venues. Nearby, notable landmarks such as an event conference venue, a sports facility stadium and a theme park enrich your travel itinerary, making it an excellent base for exploring Windsor’s lively cultural scene.
  • Walkerville: Situated in the heart of Windsor, Walkerville provides a charming mix of romantic, outdoor and city-themed experiences. This neighbourhood invites you to immerse yourself in its dynamic offerings, featuring a theatre, an arena entertainment facility and scenic hiking trails. The area is also graced by significant local attractions including a sports facility stadium, a quaint town neighbourhood and a picturesque lake, perfect for those seeking both relaxation and adventure.
  • Bridgeview: Bridgeview is a delightful neighbourhood in Windsor renowned for its family-friendly, romantic and city-themed ambience. The local attractions include a water park, theatre and educational venues that cater to diverse interests. Additionally, visitors will appreciate the close proximity of distinguished landmarks such as a sports facility stadium, an event conference venue and a convention centre, making Bridgeview an appealing destination for a well-rounded holiday exploration.

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 January to March tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.3°F (-3.7°C)Light RainMostly CloudyLowAverage
February26.2°F (-3.2°C)Light RainMostly CloudyLowSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyLowSlightly 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 SunnyAverageSlightly Low
December32.9°F (0.5°C)Light RainMostly CloudyAverageAverage

Booking with Stayz is a breeze

Are you hoping to make savings on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable discounts by opting for a longer stay. To discover a Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday accommodation.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board offers a user-friendly platform to plan new trips, resume from where you last stopped, or review and manage your itineraries. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Delight in the riverfront landscape of Windsor

Enjoy the live music and other features of Windsor. Revered for its casino gaming, riverfront and gardens, this city is both cosmopolitan and scenic. Ford Field and Little Caesars Arena are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Windsor

Are you hoping to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Windsor has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 Zoo (12.8 mi / 20.6 km)
  • Red Oaks Waterpark (14.6 mi / 23.5 km)

Exploring the natural landscape of Windsor

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor is a great place to get out in nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Windsor Riverfront (0.5 mi / 0.8 km)
  • Detroit Riverwalk (1 mi / 1.7 km)
  • Campus Martius Park (1.3 mi / 2 km)
  • Belle Isle Beach (3.7 mi / 5.9 km)
  • Heritage Park (12.8 mi / 20.6 km)
  • Lake Erie Metropark (18.5 mi / 29.8 km)

Transport options to and around Windsor

The nearest airport is in Windsor, ON (YQG), located 4.8 mi (7.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to 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 serving the city is Windsor Station.

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, Ontario, a popular area to stay is along the waterfront, particularly near the picturesque neighbourhood of Walkerville. This charming area is known for its historic architecture and vibrant arts scene, making it an appealing choice for visitors. Here, you can find a variety of properties, from stylish apartments to quaint homes, often with stunning views of the Detroit River.Another fantastic option is the downtown area, which offers a lively option with various dining and entertainment choices. Staying in this bustling part of Windsor puts you close to attractions such as the Windsor Sculpture Park, where you can enjoy an outdoor gallery of impressive sculptures along the riverfront, and the Canadian Club Brand Centre, which provides fascinating insights into the history of Canadian whisky.
Where are the best areas for renting a beach house in Windsor?
For renting a beach house in Windsor, Ontario, the area along the waterfront near the Detroit River is an excellent choice. The neighbourhood around Riverside Park offers a picturesque setting with easy access to the riverfront, where visitors can enjoy scenic views and leisurely strolls. Many properties in this region boast amenities such as spacious outdoor decks, barbecue facilities, and fully equipped kitchens, ideal for families or groups looking to enjoy a relaxed atmosphere.Another great option is the neighbourhood of Walkerville, which combines historical charm with modern conveniences. Here, you may find unique rentals that offer character, with some properties featuring private gardens, patios, and proximity to local cafes and shops. The close-knit community vibe enhances the experience, allowing guests to immerse themselves in the local culture while enjoying the waterfront.For those interested in outdoor activities, the nearby Ojibway Prairie Provincial Nature Reserve provides opportunities for hiking and wildlife watching, making it a fantastic complement to a beach house rental.
What is the most popular type of holiday rental accomodation in Windsor?
In Windsor, apartments are the most popular type of holiday rental, with approximately 225 available throughout the city. These apartments are often found in lively neighbourhoods close to the waterfront, providing easy access to attractions such as the Windsor Sculpture Park and the iconic Caesars Windsor. Most units come equipped with fully functional kitchens, spacious living areas, and many feature balconies or terraces that allow guests to enjoy the views of the Detroit River.For those seeking more space, there are around 207 holiday houses available, which tend to offer multiple bedrooms, private gardens, and outdoor seating areas—ideal for families or groups looking to relax after a day of exploring. Additionally, there are about 21 condos available, which typically provide modern amenities and convenient locations.
Are there any family house rentals in Windsor?
In Windsor, Ontario, there are numerous family-friendly house rentals available, with around 52 options to choose from. This vibrant city offers a variety of neighbourhoods suitable for families, including Riverside and South Windsor, both of which provide easy access to parks and recreational facilities. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor spaces for children to play.Travellers can expect amenities such as Wi-Fi, air conditioning, and sometimes even backyards with BBQ facilities, making it a convenient choice for family gatherings. Nearby attractions like the beautiful Windsor Riverfront, where families can enjoy walking paths and playgrounds, and the Canadian Aviation Museum add to the appeal of the area.
Can I rent a holiday home with a pool or hot tub in Windsor?
In Windsor, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing option for travellers seeking relaxation and comfort. The city offers a variety of neighbourhoods where these properties can be found, including those near the waterfront and popular parks, providing scenic views and a pleasant atmosphere.Visitors can expect a range of amenities in these rentals, such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, suiting families or groups looking to unwind. Some properties may also include additional features like barbecue facilities and spacious gardens, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Windsor?
In Windsor, there are numerous pet-friendly house rentals available, with around 53 options to choose from. These properties typically offer amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy fresh air. Many rentals are located in neighbourhoods that provide easy access to parks and green spaces, allowing for leisurely walks and playtime with your furry friends.The Riverside area, for instance, features homes close to the waterfront, great for those who enjoy scenic strolls along the Detroit River. Additionally, rentals in the South Walkerville neighbourhood often have larger yards, making them suitable for pets.
Are there any remote work holiday rentals in Windsor?
In Windsor, Ontario, there are numerous options for remote work holiday rentals, with approximately 381 available throughout the city. Many of these properties cater specifically to the needs of remote workers, offering amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable desks within the accommodations.Travellers can expect a variety of housing types, from modern apartments in downtown areas to charming homes in quieter neighbourhoods. Many rentals also come equipped with essential facilities, including fully stocked kitchens, laundry services, and spacious living areas to ensure a comfortable stay.Windsor itself has a vibrant setting, with proximity to the beautiful waterfront along the Detroit River, parks, and local attractions like the Canada South Science City and the historic Walkerville district. This makes it not only a practical choice for remote work but also an enjoyable place to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Windsor?
In Windsor, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also offer onsite parking, providing convenience for travellers with vehicles. Additionally, rentals often feature coffee and tea makers for those who appreciate a hot beverage in the morning, as well as desks for business travellers needing a workspace. Furthermore, a number of accommodations are pet-friendly, making it easier for guests to bring their furry companions along.
When is the best time to visit Windsor for a holiday rental?
July is the most popular time to visit Windsor, Ontario, as it welcomes a lively influx of tourists looking to enjoy the vibrant summer atmosphere. During this peak season, visitors can indulge in a variety of outdoor activities, from exploring the scenic waterfront parks along the Detroit River to experiencing the cultural events and festivals that take place throughout the month. The warm weather, with temperatures typically ranging from 20 to 30 degrees Celsius, sets the great stage for enjoying al fresco dining and leisurely strolls along the riverfront.If you're seeking a quieter experience, consider planning your visit in October. This month, while outside the bustling summer season, offers a beautiful display of autumn foliage, making it an ideal time for picturesque walks and local explorations. With fewer crowds, you can enjoy the charm of Windsor at a relaxed pace and still find excellent holiday rental options at great prices.
What are the top attractions in Windsor?
In Windsor, Ontario, visitors can explore several top attractions that highlight the city's charm and culture. The waterfront along the Detroit River offers scenic views and is home to the Windsor Sculpture Park, featuring a collection of outdoor artworks. This area is superb for leisurely strolls and picnics.The historic Walkerville neighbourhood is another highlight, known for its charming streets and vibrant setting. Here, travellers can visit the Hiram Walker Distillery, where they can learn about the whisky-making process and enjoy tastings.For those interested in history, the Canadian Club Brand Centre provides insights into the heritage of Canadian whisky and the city's role in its production. Additionally, the Windsor-Essex region is renowned for its wineries, making it an excellent destination for wine enthusiasts looking for tours and tastings.Finally, the nearby Ojibway Park offers nature trails and wildlife viewing opportunities, providing a lovely escape for outdoor lovers.
Are all fees included in the Windsor holiday homes prices shown on Stayz?
Stayz 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.
Are there any Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Stayz, 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.
Can I change or cancel my Windsor holiday home booking on Stayz?
To find Windsor holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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