Windsor Vacations

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Your Windsor Vacation

When you book a vacation package to Windsor, all the organizing is taken care of beforehand. This gives you more time to discover some of the best things about this riverfront city, such as its cosmopolitan vibe, diversity and friendly locals. You'll want to sightsee during your trip to Windsor. Carve out some time for big-name attractions such as Detroit Windsor Tunnel, Caesars Casino and Caesars Windsor. Expedia is here to help you escape your routine. Tailor your vacation to Windsor to suit your travel style, whatever that may look like.

Where to stay in Windsor

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

Discover the most popular places to visit in Windsor

What to do in Windsor

Windsor Hotel Deals

Best Western Plus Waterfront Hotel

Best Western Plus Waterfront Hotel

2.5 out of 5
277 Riverside Drive West Windsor ON
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $80 total per night from Jan 25 to Jan 26
$80 total
Jan 25 - Jan 26
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
Very nice place.

Reviewed on Jan 11, 2026

Best Western Plus Waterfront Hotel
Caesars Windsor - A Caesars Rewards Destination

Caesars Windsor - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
$146 nightly
The price is $174 total per night from Jan 14 to Jan 15
$174 total
Jan 14 - Jan 15
Total with taxes and fees
8.6/10 Excellent! (3,206 reviews)
Yes it was a great stay clean room and friendly staff

Reviewed on Jan 10, 2026

Caesars Windsor - A Caesars Rewards Destination
DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

4 out of 5
333 Riverside Dr W Windsor ON
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $137 total per night from Feb 8 to Feb 9
$137 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,062 reviews)
Staff very helpful and informative

Reviewed on Jan 9, 2026

DoubleTree by Hilton Windsor Hotel & Suites
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.

Find the Best Windsor Vacation Packages

Things to do in and around Windsor

Windsor, Ontario, offers a delightful mix of activities for romantic getaways, family vacations, and city-themed adventures. Enjoy fun outings at local theaters, explore educational venues, or spend relaxing days at the water park. Don't miss the chance for romantic beach strolls and sun-soaked beach days, making Windsor an ideal destination for memorable experiences and day outings that cater to all interests.

Shopping

Windsor offers great shopping at Devonshire Mall, featuring a variety of stores in a vibrant atmosphere. If you're up for a drive, head to Tecumseh Mall, which provides additional shopping options and a range of dining experiences for a delightful day out.

Recreation

Experience tranquility at Seacliff Park, a beautiful recreation area offering serene landscapes and relaxation spots. Enjoy outdoor activities and take in the fresh air. For golf enthusiasts, Ambassador Golf Club provides a fantastic outdoor setting, while Chrysler Theatre offers a cultural escape with captivating shows and entertainment.

Adventure

Experience thrills at Adventure Bay Family Water Park, where you can splash around in water slides and pools. For a scenic hike, explore the Mic Mac Park Walking Trails and East Riverside Park Trails, where you can enjoy nature and outdoor adventure amidst beautiful scenery.

Nightlife

Windsor's nightlife is vibrant, with countless options. Start your evening at the lively The Cook's Shop for great food and drinks. For dancing, check out The Coliseum, a popular club. If you prefer a laid-back vibe, the Windsor Beer Exchange offers a relaxed atmosphere with craft brews.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Windsor

Windsor, Ontario, is perfect for romantic getaways, city-themed trips, and family vacations. Explore popular attractions such as urban parks, vibrant streets, and entertainment arenas that cater to a variety of interests. Whether you're seeking family-friendly activities, outdoor adventures, or a taste of city life, Windsor offers a diverse range of experiences for every traveler to enjoy.

  • Detroit Windsor Tunnel: Experience the bustling city vibes as you travel through this unique underground tunnel connecting Windsor and Detroit. This engineering marvel offers a quick and scenic route, providing a glimpse of the vibrant culture on both sides of the border.
  • Ambassador Bridge: As a historic landmark, the Ambassador Bridge showcases stunning architectural design while connecting Windsor to Detroit. It’s a significant cultural symbol, offering a beautiful view of the Detroit skyline and the surrounding waterways.
  • Windsor Riverfront: This urban park is perfect for families and outdoor enthusiasts alike. With scenic walking paths, playgrounds, and green spaces, the Windsor Riverfront offers a relaxing atmosphere to enjoy the stunning views of the Detroit River and city skyline.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostly CloudySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudySlightly LowSlightly Low
March36.3°F (2.4°C)Light RainMostly CloudyAverageSlightly Low
April46.8°F (8.2°C)Light RainMostly SunnyAverageAverage
May59.4°F (15.2°C)Light RainMostly SunnySlightly HighAverage
June68.9°F (20.5°C)Light RainMostly SunnyAverageSlightly High
July74.1°F (23.4°C)Light RainMostly SunnySlightly HighAverage
August72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
September66.6°F (19.2°C)Light RainMostly SunnyAverageSlightly High
October54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
November41.9°F (5.5°C)Light RainMostly SunnyAverageAverage
December32.9°F (0.5°C)Light RainMostly CloudySlightly LowAverage

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.

Windsor Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Windsor Airport (YQG)
Population
278,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Adventure Bay Family Water Park, Chrysler Theatre and Walkerville Brewery

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Frequently asked questions

How much does a Windsor vacation 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 vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation package, consider planning a trip in December, January and February. You'll usually find lower prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
Windsor vacations come in various shapes and sizes, but to really sink your teeth into this place, we'd say 2 days is a good ballpark. This will mean you can fit in headline attractions like Walkerville Brewery and Windsor Community Museum and seek out some underrated gems. Don't miss out on neighborhoods such as Sandwich Towne and South Central either. If you plan wisely, you can even allow for a day trip from Windsor too.
Is it worth booking a vacation package to Windsor?
Windsor has everything you need for an amazing escape. Begin your Windsor vacation on a high note by visiting popular 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 personalize 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 vacation as a package?
Expedia vacation 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 customized Windsor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation 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 when to go: Check your schedule and get packing. Your favorite season and the activities on offer will also help you decide when to visit Windsor.
  2. Set your budget: Factor in expenses such as food, flights and transportation when calculating how much to put aside for your trip to Windsor. Then, choose a hotel that fits your budget, whether that's a low-cost stay or a deluxe getaway.
  3. Explore Windsor with Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Windsor. You can also save your must-visit places, collaborate with friends and family and organize all your plans in one place.
  4. Decide your trip length: Think about how long you want to spend exploring Windsor. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to find a Windsor vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the highlights of Windsor. Find all the fun things to do in Windsor with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Windsor vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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