Windsor holiday rentals

We found 337 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Windsor by choosing from 108 houses, 88 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:30 Oct - 6 Nov

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

Beach
9.8 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

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

Kingsville

12% off
Price is AU$4,137
for 7 nights, 1 cottage
AU$591 per night
includes taxes & fees
Prepare to fall in love with this adorably tropical beach front property!

Find spaces that suit your style

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 Detroit Windsor Tunnel 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)
  • Chandler Park Golf Course (6.5 mi / 10.5 km)
  • Detroit Golf Club (9 mi / 14.4 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)
  • Civic Center Park (16.5 mi / 26.6 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 home?
Stay in a holiday home in Walkerville and you'll be based in one of Windsor's leading areas. Walkerville Brewery and Willistead Park Trail Trailhead are two top attractions here that'll keep you entertained during your visit.
What is the most popular type of holiday home accommodation in Windsor?
Apartments are the most popular style of holiday home in Windsor, according to our data. Even if you have something a little different in mind, Stayz has properties in loads of shapes and sizes. Browse our many options to find your ideal match.
How much does it cost to rent a holiday home in Windsor?
Season, property type and length of stay are some of the things that can influence the price of a holiday home. Simply enter your travel dates to find the ultimate escape. From cosy chalets to expansive luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Windsor?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Type in your Windsor travel dates to see all your options on Stayz. Can't live without a hot tub, or maybe a private pool? Use our filters to pick the amenities and features you need.
Are there pet-friendly holiday homes in Windsor?
With 29 holiday homes that allow pets, your furry little friend can join in on your Windsor getaway. Use the filter tool to browse our pet-friendly holiday homes and find a stay that'll set tails wagging on Stayz.
Can I rent a house with a pool in Windsor?
Pack your swimming gear and pool noodle, because there are three houses with a private pool in Windsor. Unwind at one of these terrific holiday homes and make every day a pool day. Simply enter your travel dates into Stayz, then check the "pool" filter to find a place to make a splash!
What are popular home amenities in Windsor?
The most popular home amenities people are looking for in Windsor include a beach view, a water view and nearby museums. Whether you're travelling with friends, family or even pets, Stayz holiday homes have the best amenities for making epic memories with the people that matter most.
Are there large group holiday homes in Windsor?
Windsor has four holiday homes that can fit 10 or more people. These stays come with the space and privacy you need to enjoy good times with friends and family.
Are there holiday homes in Windsor that welcome kids?
Windsor has 28 family-friendly holiday homes to choose from. And securing a stay that welcomes kiddos is easy with Stayz's "Properties good for families" filter. As well as having the whole place to yourselves, you'll also get conveniences and perks like extra bedrooms, full kitchens and private pools.
What are the top attractions for families in Windsor?
You'll find lots of exciting things to see and do with the family in Windsor, including:

  • Adventure Bay Family Water Park
  • Windsor Community Museum
  • Art Gallery of Windsor

Are there one-bedroom holiday homes in Windsor?
Yes, you'll find nine one-bedroom properties in Windsor to select from. A one-bedroom holiday property is a great choice if it's only you and your partner or if you're holidaying solo. Add in more space, privacy and convenience than a standard hotel, and you've got the makings of a break to remember.
Can I find two-bedroom holiday homes in Windsor?
Take off with your besties and experience complete comfort and privacy in one of the 12 two-bedroom holiday properties Windsor has to offer.
Are there holiday homes with WiFi in Windsor?
You can pick from 14 holiday homes with WiFi in Windsor. If you'd like to disconnect from daily life on your holiday, but still need to be connected to the web, these getaways have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Windsor?
You'll find 25 Stayz holiday homes with air conditioning in Windsor offering that cool, cool breeze and extra level of comfort. Just enter your dates of travel and then take advantage of our filter tool to help you locate properties with air conditioning.
How old do you have to be to rent a holiday home in Windsor?
The minimum age is usually 16, 18 or 21. It can vary from property to property on Stayz, so look at the rules of your preferred Windsor holiday home before booking.
How long can I rent a holiday home in Windsor for?
It really depends on the Windsor property. To browse available options offering extended stays, simply enter your dates and number of guests into Stayz. Look forward to having the entire property to yourself, along with comforts such as air conditioning, a kitchen and outdoor spaces where the kids can burn off energy. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.