Windsor Holidays
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Where to stay in Windsor
Downtown Windsor
City centre Windsor pulses with energy where casino lights meet the Detroit River waterfront. The Caesars Windsor casino complex anchors this entertainment district, surrounded by lively bars and diverse restaurants. Cultural attractions like the Art Gallery of Windsor and Capitol Theatre showcase the city's artistic side. Stroll along the scenic Windsor Riverfront Trail for breathtaking views of Detroit's skyline. Dieppe Gardens offers peaceful green space perfect for escaping the city centre bustle. Visitors can easily explore attractions like the Windsor Community Museum or catch performances at the Chrysler Theatre. The neighborhood's multicultural dining scene reflects Windsor's heritage, with options ranging from casual cafes to upscale establishments.
Walkerville
Walkerville, a historic gem founded by Hiram Walker, offers a delightful blend of Victorian architecture and modern charm. Red brick facades and ornate heritage buildings line tree-canopied streets. The area centers around Willistead Manor with its manicured gardens and Tudor-Jacobean design. This walkable district features unique boutiques and craft breweries housed in century-old shopfronts. Visitors can explore the historic Hiram Walker Distillery complex with its iconic brick buildings. Local cafes and artisanal shops create a village-like atmosphere that showcases authentic Canadian life away from city centre Windsor.
Riverside
Riverside offers a peaceful retreat along the Detroit River where quiet residential streets meet scenic waterfront paths. This family-oriented Windsor area showcases mid-century homes with well-kept lawns and mature trees. Enjoy stunning views of Detroit's skyline while strolling through Riverside Park. The area provides an authentic slice of suburban Canadian life away from tourist crowds. Windsor Family Credit Union Centre and walking trails along Lake Saint Clair offer recreation options for visitors. Though limited in dining and shopping, Riverside's charm lies in its genuine local atmosphere and riverfront beauty.
South Windsor
South Windsor offers a peaceful family-oriented retreat from Windsor's busy city centre. Tree-lined streets showcase brick homes with tidy lawns. Parks like Oakwood Community and the Recreation Complex provide green spaces with walking trails and sports facilities. Budget-friendly chain hotels and holiday rentals make this area attractive for cost-conscious travellers. A car is recommended as public transit is limited. The area provides an authentic suburban Canadian experience with easy access to Windsor's attractions.
City Centre
City Centre in Windsor combines business energy with scenic waterfront charm along the Detroit River. The sleek skyline features glass office towers and the iconic Caesars Windsor casino. Stroll the riverfront promenade for stunning views of Detroit across the water. Adventure Bay Family Water Park offers family fun while culture seekers can explore the Chrysler Theatre and Windsor Community Museum. Cross the Detroit Windsor Tunnel to experience Michigan attractions just minutes away. Dieppe Gardens provides a peaceful retreat from the city centre bustle.
Discover the most popular places to visit in Windsor
What to do in Windsor
Explore Downtown Detroit Walking Tour: Architecture+History
Roasting Experience at 14th Coffee Co
Downtown Detroit Walking Tour: History & Iconic Landmarks
Windsor Hotel Deals
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites
DoubleTree by Hilton Windsor Hotel & Suites
Holiday Inn Express Windsor Waterfront by IHG
Holiday Inn Express Windsor Waterfront by IHG"Could do more to accommodate a request. I booked two rooms under one name, when I when there we were totally separated and they were not accommodating to get us in the same floor. Was disappointed because the kids wanted to be together with the friends. Reception was not helpful at all. I was told it has to be under one name to accommodate my request. The breakfast was ok compared other holiday inns."
Hampton Inn & Suites by Hilton Windsor
Hampton Inn & Suites by Hilton Windsor
Best Western Plus Waterfront Hotel
Best Western Plus Waterfront Hotel
Quality Inn & Suites Downtown Windsor
Quality Inn & Suites Downtown Windsor"Property is conveniently located downtown close to plenty of restaurants and establishments and not too far from the river walkway Rooms are quiet and pretty spacious Friendly staff"
Comfort Inn & Suites Ambassador Bridge
Comfort Inn & Suites Ambassador BridgeFind out more about Windsor
Things to do in Windsor
Windsor, Ontario, offers a delightful mix of activities perfect for romantic getaways, family holidays, or city explorations. Highlights include the captivating theatre scene and a fantastic water park, alongside the unique attraction of LEGOLAND Windsor. Whether you're seeking an exciting staycation or simply wish to explore this vibrant city, Windsor promises memorable experiences for all visitors.
Shopping
The nearest shopping destination is Devonshire Mall, where you can explore a variety of high street shops, local boutiques, and dining options. If you're up for a drive, consider visiting the nearby Tecumseh Mall for more shopping choices and a vibrant atmosphere.
Recreation
The Chrysler Theatre offers captivating performances, blending romance and culture for an enriching evening. For outdoor enthusiasts, the Ambassador Golf Club provides a serene golfing experience amidst beautiful landscapes. Alternatively, enjoy a film at Landmark Cinemas Windsor, perfect for family outings or a romantic night in.
Adventure
Adventure Bay Family Water Park offers thrilling water slides and fun-filled family activities, perfect for a day of excitement. For nature enthusiasts, Odette Sculpture Park Walking Trail and East Riverside Park Trails provide picturesque hiking routes with stunning scenery, ideal for outdoor adventures and serene exploration.
Nightlife
In Windsor, experience vibrant nightlife at venues like the iconic Caesars Windsor, which offers gaming and live entertainment. Explore the lively bars along Ouellette Avenue, where you can enjoy craft cocktails and live music, creating a lively atmosphere perfect for a memorable night out.
Find the best attractions in Windsor
Windsor, Ontario, offers a delightful blend of romantic, city-themed, and family-friendly experiences. Explore popular attractions such as the Windsor Racecourse, Windsor Great Park, Royal Windsor, and the iconic Windsor Castle. With a variety of street and urban parks, as well as entertainment facilities, there's something for everyone seeking outdoor adventures or urban exploration in this charming city.
- Detroit Windsor Tunnel: Experience the vibrant city atmosphere as you cross this bustling thoroughfare connecting Windsor to Detroit. The tunnel is renowned for its unique urban charm and offers a glimpse into the dynamic life of both cities.
- Ambassador Bridge: This iconic structure is not only a vital trade link but also a symbol of cultural exchange. Walking along or viewing the bridge provides a profound appreciation of its historical significance and architectural grandeur.
- University of Windsor: Explore this esteemed institution that boasts a rich history and a vibrant cultural scene. The campus is home to stunning architecture and offers engaging events that reflect the diverse community spirit.
Best time to go to Windsor
The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.
Tips to save on your trip to Windsor
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Windsor.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.
Frequently Asked Questions
How much does a Windsor holiday package cost?
You'll find cheap prices on Expedia for your Windsor getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor holiday package, consider visiting in January, February and April. You'll generally find lower rates on hotels and airfares during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windsor?
To fully enjoy your Windsor holiday, we suggest staying for 2 days. Split your time between discovering Chrysler Theatre, Walkerville Brewery and other well-known attractions, as well as experiencing neighbourhoods like East Windsor and Walkerville. If you've got some time to spare, include a day trip in your Windsor holiday itinerary.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an unforgettable getaway. Get your Windsor holiday off to a flying start by checking out top attractions like Adventure Bay Family Water Park.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you're considering a spontaneous Windsor getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Windsor?
- Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Windsor.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodation will probably be the largest expense during your trip to Windsor.
- Decide how long to go for: Now that you know more about Windsor, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Windsor holiday package that brings all your bookings together.