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A city skyline with a prominent casino building, a tall skyscraper, and several other high-rise buildings along a waterfront.

Windsor Holidays

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Where to stay in Windsor

Find the best Windsor areas for the activities you enjoy most. Learn more about Windsor
Learn more about Windsor
A city skyline at dusk with illuminated buildings reflecting on the water.

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.

A historic stone building with a red roof, surrounded by trees and a Canadian flag.

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.

A sunset over a city skyline with a body of water in the foreground.

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.

A cargo ship on a river with a bridge and industrial buildings in the background.

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.

A frozen river with a city skyline in the background.
Photo by Mohammad elsawi
Open Photo by Mohammad elsawi

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

A nighttime view of a hotel with a moon in the sky, a waterfall, and illuminated steps leading to the building.
Photo by Daniel J Bellyk
Open Photo by Daniel J Bellyk

Caesars Casino

8.4/10 (1,170 reviews)
This glittering riverside casino features 100,000 square feet of gaming space with over 2,500 slot machines. Reserve tickets to The Colosseum where international performers take the 5,000-seat stage.

What to do in Windsor

Detroit Tigers Baseball Game at Comerica Park

Detroit Tigers Baseball Game at Comerica Park

S$30
per adult
0% of travellers recommend
Detroit Tigers Baseball Game at Comerica Park
See all activities in Windsor

Windsor Hotel Deals

Premium bedding, pillow-top beds, in-room safe, desk

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
4.0 star property
0.7 km from Windsor
8.6 out of 10, Excellent, (3,329 reviews)
"Big room and great, comfortable bed! Property is huge and takes a bit of self-orienting to figure out where things are."
The price is S$97
includes taxes & fees
17 Aug - 18 Aug
Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Windsor

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Book with confidence

Things to do in Windsor

Windsor is an ideal destination for romantic getaways, family holidays, and city adventures. Visitors can enjoy a variety of activities, including educational attractions and theatre performances. A standout experience is the Legoland Windsor, perfect for families seeking fun and excitement. Consider an awesome staycation at Legoland Windsor for an unforgettable holiday filled with creativity and adventure.

Shopping

For a delightful shopping experience in Windsor, visit Devonshire Mall, where you’ll find a mix of fashion, entertainment, and family-friendly options. If you're up for a drive, the nearby Tecumseh Mall offers even more retail choices and local shops to explore.

Recreation

Experience captivating performances at Chrysler Theatre, where romance and culture entwine. Enjoy a relaxing day at Ambassador Golf Club, surrounded by picturesque greens and outdoor sports. Alternatively, unwind at Landmark Cinemas Windsor, perfect for family entertainment and romantic movie dates.

Adventure

Adventure Bay Family Water Park offers thrilling water slides and wave pools, perfect for family fun and excitement. For a dose of nature, explore the Odette Sculpture Park Walking Trail and East Riverside Park Trails, both featuring stunning outdoor scenery and adventurous hiking opportunities.

Nightlife

Windsor's nightlife is vibrant, with an array of bars and clubs. Visit The Loop, known for its lively atmosphere and cocktails. For a more relaxed vibe, try The Windsor Beer Exchange, where you can enjoy local brews and live music, making for an unforgettable evening out.

Find the best attractions in Windsor

Windsor, Ontario, is perfect for romantic getaways, city explorations, and family vacations. Visitors can enjoy a variety of attractions, including the Royal Windsor, Windsor Great Park, Windsor Castle, and Windsor Racecourse, all set within charming streets and urban parks. This city offers a delightful mix of outdoor experiences and urban entertainment, catering to diverse interests and ensuring a memorable visit for all types of travellers.

  • Detroit Windsor Tunnel: Experience the bustling city vibes of the Detroit Windsor Tunnel, a vital connection between Windsor and Detroit. This underground passage offers a unique perspective of urban life as you travel beneath the river, making it a fascinating journey for tourists.
  • Ambassador Bridge: The Ambassador Bridge is a historic landmark that showcases the rich cultural heritage of the area. Spanning the Detroit River, this iconic bridge not only facilitates trade but also offers stunning views and a glimpse into the region's history.
  • University of Windsor: A historic institution, the University of Windsor boasts beautiful architecture and a vibrant campus life. Explore its cultural vibes through various events and exhibitions, making it a great spot for both education and leisure.

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

  • 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 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.