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

Windsor Holidays from £1,078

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Top Windsor flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 20 Aug - 24 Aug

    Trumbull and Porter Hotel + Flight

    Corktown
    4 nights
    3.5 star property
    8.4/10 - Very good (1,184 reviews)
    Return London (LHR) - Detroit (DTW)
    LHR - DTW1 stop DTW - LHR1 stop
    £1,262
    £1,078
    per traveller
    found 12 hours ago
    Trumbull and Porter Hotel
  • 20 Aug - 24 Aug

    The Townsend Hotel + Flight

    Birmingham
    4 nights
    4.0 star property
    9.2/10 - Wonderful (772 reviews)
    "The staff is the best part about staying at the Townsend. This is old money. They have incredibly well trained staff and just plain knowledgeable, helpful, and kind people. If you're looking for a great experience in Birmingham, stay here!"
    Reviewed July 16, 2026
    Return London (LHR) - Detroit (DTW)
    LHR - DTW1 stop DTW - LHR1 stop
    £1,495
    £1,243
    per traveller
    found 12 hours ago
    The Townsend Hotel
  • 20 Aug - 24 Aug

    Daxton Hotel Birmingham, Curio Collection by Hilton + Flight

    Birmingham
    4 nights
    4.0 star property
    9.2/10 - Wonderful (599 reviews)
    Return London (LHR) - Detroit (DTW)
    LHR - DTW1 stop DTW - LHR1 stop
    £1,645
    £1,443
    per traveller
    found 12 hours ago
    Daxton Hotel Birmingham, Curio Collection by Hilton
  • 20 Aug - 24 Aug

    MotorCity Casino Hotel + Flight

    North Corktown
    4 nights
    4.5 star property
    8.8/10 - Excellent (4,728 reviews)
    Return London (LHR) - Detroit (DTW)
    LHR - DTW1 stop DTW - LHR1 stop
    £1,353
    £1,228
    per traveller
    found 12 hours ago
    MotorCity Casino Hotel
  • 20 Aug - 24 Aug

    Hotel Indigo Detroit Downtown by IHG + Flight

    Downtown Detroit
    4 nights
    3.5 star property
    8.4/10 - Very good (1,283 reviews)
    "Good location. No 'store' to get sunscreen, etc. Bar was closed on a Saturday afternoon."
    Reviewed July 17, 2026
    Return London (LHR) - Detroit (DTW)
    LHR - DTW1 stop DTW - LHR1 stop
    £1,596
    £1,453
    per traveller
    found 12 hours ago
    Hotel Indigo Detroit Downtown by IHG

Where to stay in Windsor

Find the best Windsor areas for the activities you enjoy most. Learn more about Windsor
Learn more about 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

Windsor Hotel Deals

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.

Frequently Asked Questions

Why should I book my Windsor holiday with Expedia?

Choose Expedia to plan your next big adventure simply and all in one place. Our top tip for bagging a great deal on a Windsor retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to worry if you have to switch up your travel plans. Round-the-clock help with cancelling and changing your trip is available via our Customer Service Portal link.

When is the best time of year to holiday in Windsor?

If you enjoy the excitement that comes with peak season, head to Windsor in May, July and August. If you're looking for a calmer vibe, December, January and February will suit you better. To give you an idea of the type of weather you can experience, the daytime average temperature in January, the coolest time of year in Windsor, is -3ºC. The warmest period here is July, when temperatures average 23ºC.

What are the top hotels for my holiday in Windsor?

If you're thinking of staying in the Walkerville neighbourhood, Best Western Plus Waterfront Hotel and Super 8 by Wyndham Windsor/Dougall are in-demand options. East Windsor is also a favourite Windsor area. We recommend Hampton Inn & Suites by Hilton Windsor or Caesars Windsor if you choose this end of town.

How do I get a cheap holiday to Windsor?

Combine your flights and hotels, throw in extras such as tours, and save with a Windsor holiday. You won't just score wonderful discounts on your escape — you'll have plenty of choice at your fingertips too. When you book with Expedia, you'll have your pick of over 400 air carriers and 321,000 properties globally. Your next epic adventure starts right here, right now! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.

What should I do on my Windsor holiday?

Make sure your next holiday in Windsor is one to remember by checking out its top attractions. Detroit Windsor Tunnel, Caesars Casino, Caesars Windsor and University of Windsor are just some of the things you should see while you're here.

What is the best area to stay in when on holiday in Windsor?

If you plan to check out Detroit Windsor Tunnel, save yourself the hassle of commuting and find somewhere to stay close by. It's one of the best attractions in Windsor.

Do I need a visa for my Windsor holiday?

Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and reason for your visit, whether it be for holidays or work, will determine if you'll need a visa for Windsor. Also double-check that your passport is up to date and has a minimum of six months validity remaining after the date of your return. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.

What should I wear on my Windsor holiday?

Think about the types of activities you'll be doing during your Windsor trip and travel with pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts. Take a look at the weather forecast so you can pack appropriately. The warmest time of year in Windsor is July, with average daytime temperatures of 23ºC. If you're visiting during the coolest month of January, the mercury averages -3ºC during the day.

What does an Expedia Windsor holiday include?

Flights, hotels and car hires, or any combination of the three — the choice is all yours! Whether you're headed to Windsor on a family road trip or travelling with your friends, there's a bundle to fit every style and budget. Once you've made your booking, why not add on one or two tours or activities? Private holiday homes and apartments are a few of the most popular property types in Windsor. Whatever your holiday style or group size, you can rely on Expedia for the freedom and flexibility to customise your next dream escape.

Does Expedia offer Book Now, Pay Later Windsor holidays?

We sure do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that suits you best during checkout and take away the stress of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying in multiple instalments works for you, pick this option at checkout.
  • No-deposit holidays: Pressing the "book now" button is easier with this payment plan. With no upfront fee for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Windsor Expedia holiday?

Yes, the choice is all yours. Expedia has access to more than 400 airlines across the globe, so you can tailor your Windsor holiday according to your needs and budget.

Book with confidence

Things to do in Windsor

Windsor offers a delightful blend of activities perfect for romantic getaways, family holidays, or city explorations. Enjoy educational experiences, captivating theatre productions, and a thrilling water park. Don't miss the chance to explore the fantastic Legoland Windsor for an unforgettable staycation that delights visitors of all ages.

Shopping

Windsor offers a delightful shopping experience with Devonshire Mall, a bustling centre filled with entertainment and family vibes. If you're up for a drive, the nearby Lakeside Shopping Centre features a variety of shops and dining options, perfect for unique gifts and souvenirs.

Recreation

Experience a round at the Ambassador Golf Club, where you can enjoy the lush greens and outdoor atmosphere. For a cultural evening, catch a performance at Chrysler Theatre, offering a blend of romance and entertainment. Alternatively, unwind with a film at Landmark Cinemas Windsor, perfect for family outings.

Adventure

At Adventure Bay Family Water Park in Windsor, enjoy thrilling water slides and wave pools, perfect for family fun. Explore the scenic Mic Mac Park Walking Trails for a refreshing hike through nature. Alternatively, discover the beautiful East Riverside Park Trails, offering picturesque views and outdoor adventure.

Nightlife

Windsor's nightlife offers vibrant experiences along Ouellette Avenue, featuring lively bars and clubs like The Loop and The Windsor Beer Exchange. Enjoy live music, dance the night away, or relax in a pub atmosphere. The waterfront also hosts charming spots for evening strolls and gatherings.

Find the best attractions in Windsor

Windsor, Ontario, offers a delightful mix of romantic escapes, urban experiences, and family-friendly activities. Visitors can explore captivating attractions like Windsor Castle, Windsor Great Park, Royal Windsor, and Windsor Racecourse. With its vibrant streets, urban parks, and entertainment venues, Windsor is perfect for those seeking outdoor adventures or city-themed outings. Enjoy the charm of this lovely city, ensuring a memorable holiday experience for every traveller.

  • Detroit Windsor Tunnel: Experience the unique thrill of crossing the Detroit Windsor Tunnel, an underground route connecting Canada and the USA. This bustling street captures the vibrant city atmosphere, with its lively surroundings showcasing the local culture and energy.
  • Ambassador Bridge: As an iconic symbol of cross-border connection, the Ambassador Bridge offers rich cultural significance. Stroll along this historic bridge, where you can appreciate its architectural beauty and the stunning views of the Detroit River, embodying the spirit of friendship between nations.
  • University of Windsor: Visit this esteemed institution, known for its lush campus and historical significance. The University of Windsor is not only a hub for education but also a centre for cultural events, making it a vibrant spot for art and community engagement.

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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.