Windsor Vacation Packages

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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.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Housing Albert
Windsor Manor
Holiday Inn Express & Suites Windsor East - Lakeshore by IHG
Caesars Windsor
Travelodge by Wyndham Windsor

Where to stay in Windsor

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

Things to do in and around Windsor

Windsor is an ideal destination for romantic getaways, family outings, and city-themed vacations. Visitors can enjoy a range of activities, including educational experiences, a fun-filled water park, and captivating theatre performances. Don't miss the chance to indulge in golf vacations and create lasting memories with loved ones in this vibrant city.

Shopping

The nearest shopping destination is Devonshire Mall, where you can enjoy a mix of high street fashion, entertainment, and local eateries. If you're up for a drive, consider visiting the nearby Tecumseh Mall for more retail options and unique finds.

Recreation

Experience a round of golf amidst the serene landscapes at Ambassador Golf Club, indulge in captivating performances at Chrysler Theatre for a taste of culture, or unwind at Seacliff Park, where you can enjoy peaceful walks and relaxation just 48.3km from Windsor.

Adventure

Experience splashes of fun at Adventure Bay Family Water Park, where thrilling slides and wave pools await. For outdoor adventure, hike the scenic trails of Mic Mac Park and East Riverside Park, immersing yourself in nature while enjoying stunning views along the way.

Nightlife

Windsor's nightlife is vibrant, featuring lively bars along Ouellette Avenue and Riverside Drive. Enjoy live music at The Windsor Beer Exchange or dance at The Essex. For a unique experience, visit The Green Room for craft cocktails and a laid-back atmosphere, perfect for unwinding after a day of exploration.

*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 an ideal destination for romantic getaways, family vacations, and urban adventures. Visitors can explore a variety of attractions, including charming streets, urban parks, and entertainment arenas. The city's points of interest cater to those seeking both family-friendly activities and outdoor experiences, providing a perfect blend of city life and leisure for every type of traveller.

  • Detroit Windsor Tunnel: Experience the hustle and bustle of city life as you traverse the Detroit Windsor Tunnel, a vital connection between Canada and the United States. This underground route offers a unique perspective on urban infrastructure, immersing you in the vibrant atmosphere of Windsor.
  • Ambassador Bridge: As one of the most iconic structures in the region, the Ambassador Bridge embodies historical significance and cultural ties. Stroll along its vicinity and take in stunning views of the Detroit River while learning about its storied past.
  • University of Windsor: Explore the beautiful campus of the University of Windsor, where history meets modern academia. Enjoy the cultural vibe and various art installations that enrich the student experience, making it a lively place to visit.

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 with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.3°F (-3.7°C)Light RainMostlySlightly LowSlightly Low
February26.2°F (-3.2°C)Light RainMostlySlightly LowSlightly Low
March36.3°F (2.4°C)Light RainMostlyAverageSlightly 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 RainMostlySlightly 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 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.

Ready to book your vacation to Windsor?

 

Choose your dates

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
The price is CA $163 per night from Aug 10 to Aug 11
CA $163
CA $195 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"The view from our room was spectacular and everything was perfect. The only issue was that there was not parking available at the hotel as described. We had to park across the street and were told the fee would be the same. It was pretty inconvenient and we were glad we didn’t have much luggage. ..."

Reviewed on Jul. 31, 2025

Best Western Plus Waterfront Hotel
Caesars Windsor

Caesars Windsor

4 out of 5
377 Riverside Dr E, Windsor, ON
The price is CA $152 per night from Sep 1 to Sep 2
CA $152
CA $207 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (3,027 reviews)
"We enjoyed our stay. Everyone was friendly and helpful. It was quite a walk to get to the reception desk. Having to walk through the casino and find the reception desk wasn't fun."

Reviewed on Jul. 30, 2025

Caesars Windsor
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
The price is CA $165 per night from Aug 10 to Aug 11
CA $165
CA $198 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Friendly staff. Jessica at reception at the time of check out (morning on July 29) was amazing, helpful and managed to procced with Expedia's phone call to cancel one night (left hotel one night earlier) since business trip work was completed ahead of time. Thank you to both Expedia and Hotel staff ..."

Reviewed on Jul. 30, 2025

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.

Discover the most popular places to visit in Windsor

What to do in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $814 on Expedia for your Windsor break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you'd like to book a cheap Windsor vacation package, consider travelling in January, February and April. You'll typically find better prices on accommodations and flights during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Windsor?
With about 2 days, you'll have plenty of time to experience popular neighbourhoods such as East Windsor and Walkerville during your Windsor vacation. Be sure to also add Caesars Windsor and Adventure Bay Family Water Park to your sightseeing list. Searching for more adventures? Consider exploring outside of Windsor on tours and day trips.
Is it worth booking a vacation package to Windsor?
It's easy to see why a Windsor vacation is on the to-do list of many travellers. Major attractions like Adventure Bay Family Water Park are just the beginning of what you can explore here.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Windsor package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays individually. Better still, you can tailor your Windsor escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates finalized, book as early as you can to score some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to vacation in Windsor.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to activities and flights. Your accommodations will likely be the biggest expense during your trip to Windsor.
  3. Decide how long to go away for: Now that you know more about Windsor, you can work out the ideal length of your break. Put together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Windsor vacation package that brings all your bookings together.

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