Windsor Holidays
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Your Windsor Holiday
Uncover the best of Windsor with a customised Windsor holiday package. From its cosmopolitan vibe and diversity to its friendly locals, you'll love experiencing this riverfront city in your own way. You'll want to take in some sights during your trip to Windsor. Find time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Check out Expedia's extensive range of travel options and book your dream holiday to Windsor now.
Our guide on 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
Downtown Detroit Walking Tour: History & Iconic Landmarks
Detroit Lions Football Game at Ford Field
Windsor Hotel Deals
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination"It was a great place to spend a special night."
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"Everything perfectly fine"
Best Western Plus Waterfront Hotel
Best Western Plus Waterfront Hotel"Stayed here while attending the Windsor International Film Festival.(WIFF) Located on the waterfront it was within walking distance of the different theatres the festival was showing at. This hotel requires that you have to swipe your room card in the elevator in order to access your floor. An excellent safety measure that all hotels should adopt. The room was well appointed with the usual ammenities, Hair dryer, coffee maker,small fridge, etc. but no microwave. Individual toiletries, bar soap,...
Hampton Inn & Suites by Hilton Windsor
Hampton Inn & Suites by Hilton Windsor
TownePlace Suites by Marriott Windsor
TownePlace Suites by Marriott Windsor
Comfort Inn & Suites Ambassador Bridge
Comfort Inn & Suites Ambassador Bridge"No elevator, the room was very dirty and dusty!"
Find out more about Windsor
Things to do in Windsor
Windsor, Ontario, is an ideal destination for romantic getaways, family holidays, and city excursions. Visitors can enjoy a variety of attractions including educational experiences, vibrant theatre performances, and fun-filled water parks. Additionally, the city offers enticing wedding packages, scenic shore excursions, and engaging day trips, ensuring a memorable stay for all types of travellers.
Shopping
Windsor offers a delightful shopping experience at Devonshire Mall, featuring a variety of shops and entertainment options. If you're up for a drive, consider visiting nearby shopping centres like Tecumseh Mall, which also boasts a range of stores and dining choices.
Recreation
Experience the Chrysler Theatre, where you can enjoy captivating performances that evoke romance and cultural enrichment. For outdoor enthusiasts, the Ambassador Golf Club offers a serene golfing experience amidst lush landscapes, perfect for relaxation and sport. Finally, unwind at Landmark Cinemas Windsor with family-friendly films in a charming setting.
Adventure
Experience the thrills of Adventure Bay Family Water Park, where water slides and wave pools await. For scenic outdoor adventures, explore the Odette Sculpture Park Walking Trail and East Riverside Park Trails, both offering stunning views and a chance to connect with nature on your hiking journey.
Nightlife
Windsor's nightlife is vibrant, centred around the bustling Ouellette Avenue, lined with lively bars, clubs, and lounges. Enjoy live music at local venues, try your luck at the Caesars Windsor Casino, or relax in pubs featuring craft beers and cocktails, offering a warm and welcoming atmosphere.
Find the best attractions in Windsor
Windsor offers a delightful blend of romantic and family-friendly experiences, making it an ideal destination for a city-themed getaway. Explore the charming streets, urban parks, and entertainment arenas. Don't miss the iconic Windsor Castle and the picturesque Windsor Bridge, which are perfect for capturing memorable moments. Whether you seek outdoor adventures or cultural attractions, Windsor has something to cater to every traveller's taste.
- Detroit Windsor Tunnel: Experience the unique atmosphere of this bustling street that connects Windsor and Detroit. The tunnel is not only a vital transport link but also a vibrant thoroughfare where you can feel the city's energy and enjoy the diverse local culture.
- University of Windsor: Immerse yourself in the rich history and academic ambiance of this esteemed institution. With its beautiful campus and cultural events, the University of Windsor offers a glimpse into the region's educational heritage and community spirit.
- Ambassador Bridge: As a historic landmark, this iconic bridge serves as a vital connection between Canada and the United States. Stroll along the nearby areas to take in stunning views and appreciate its architectural significance.
Best time to go to Windsor
The best time to visit Windsor is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.
Tips to save on your trip to Windsor
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
- Consider traveling to Windsor during the low season (January to March) for more affordable options.
- 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.