Windsor Vacations from $1,020

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Dream Estate Inn

Dream Estate Inn

3.5 out of 5
Price was $1,108, price is now $1,020 per person
$1,020
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
9.4/10 Exceptional! (142 reviews)
Turn in to property driveway is awkward when approaching from WB Seacliffe and borderline unsafe when coming EB from the roundabout. Remember- Leamington drivers can often be unpredictable.

Reviewed on Oct 19, 2026

Hotel STRY

Hotel STRY

2 out of 5
Price was $1,180, price is now $1,049 per person
$1,049
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
10/10 Exceptional! (46 reviews)
I almost don’t want to share how spectacular Hotel STRY is! I will make a point to book this hotel every single time I am in this area. I will drive from Windsor just to stay here. If you have the pleasure of meeting Cat, she is amazing and will take care of all your needs. This is a Must Stay if you are anywhere near Amherstburg!

Reviewed on Oct 30, 2026

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

Holiday Inn Express & Suites Windsor East - Lakeshore by IHG

2.5 out of 5
Price was $1,080, price is now $1,021 per person
$1,021
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
9.6/10 Exceptional! (1,003 reviews)
0

Reviewed on Nov 4, 2026

Days Inn by Wyndham Leamington

Days Inn by Wyndham Leamington

2.5 out of 5
Price was $1,078, price is now $1,045 per person
$1,045
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
7.8/10 Good! (1,001 reviews)
Great stay, clean room, amazing staff and good location

Reviewed on Nov 6, 2026

Quality Inn

Quality Inn

2.5 out of 5
Price was $1,114, price is now $1,088 per person
$1,088
per person
Dec 14 - Dec 17
found 3 hours ago
Roundtrip flight included
Orange County (SNA) to Windsor (YQG)
8.6/10 Excellent! (534 reviews)

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Where to stay in Windsor

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

Downtown Windsor

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Windsor, Detroit Windsor Tunnel and The Colosseum at Caesars Windsor are top sights worth seeing.

Find hotels in Downtown Windsor

Stay near popular Windsor attractions

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.
See properties

What to do in Windsor

Detroit Guided Pedicab Tour Explore the City in Comfort

Detroit Guided Pedicab Tour Explore the City in Comfort

$125
per traveler
Detroit Guided Pedicab Tour Explore the City in Comfort
See all activities in Windsor

Windsor Hotel Deals

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination

4 out of 5
377 Riverside Dr E Windsor ON
$60 nightly
The price is $71 total per night from Dec 8 to Dec 9
$71 total
Dec 8 - Dec 9
Total with taxes and fees
8.8/10 Excellent! (3,634 reviews)
"Great stay."

Reviewed on Nov 8, 2026

Caesars Windsor Hotel & Casino - A Caesars Rewards Destination
Comfort Inn & Suites Ambassador Bridge

Comfort Inn & Suites Ambassador Bridge

2.5 out of 5
2330 Huron Church Rd Windsor ON
Fully refundable
$63 nightly
The price is $75 total per night from Dec 6 to Dec 7
$75 total
Dec 6 - Dec 7
Total with taxes and fees
8.2/10 Very Good! (1,646 reviews)
"Super petit déjeuner, lit très confortable"

Reviewed on Nov 8, 2026

Comfort Inn & Suites Ambassador Bridge
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
$95 nightly
The price is $114 total per night from Nov 15 to Nov 16
$114 total
Nov 15 - Nov 16
Total with taxes and fees
8.4/10 Very Good! (1,407 reviews)
"Great location right downtown and price is reasonable. Property is showing some age but it does appear that some floors are being renovated."

Reviewed on Nov 8, 2026

Best Western Plus Waterfront Hotel
See all 431 properties in Windsor
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

What is the best time to go to Windsor?
The best time for a Windsor vacation package is from June to July, when the city experiences very warm to hot and humid weather, making it ideal for enjoying outdoor activities and festivals. These months are also the busiest for travelers.

For those seeking a quieter experience, January and February are the lowest demand months, though winters in Windsor are cold. November also sees fewer visitors.
How can I save money on a Windsor vacation package?
When you bundle, you can save up to 30%*. To save money on a Windsor package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's included in a Windsor vacation package?
A Windsor vacation package typically bundles round-trip flights, hotel stays, and rental cars. As a central urban destination, Windsor's many hotels offer convenient access to city attractions. Many properties also provide airport shuttle service to and from Detroit Metropolitan Wayne County Airport (DTW), and a good number include free breakfast, which can be a practical saving during your trip.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Windsor?
For families, a Windsor vacation package with a stay at the 3.5-star Holiday Inn & Suites Windsor Ambassador Bridge by IHG is a strong choice, offering family rooms, an indoor pool, and a restaurant.

Couples seeking a romantic getaway might consider a package built around the Hyatt Place Windsor, rated 8.8 out of 10. This hotel features a bar and lounge, an indoor pool, and a restaurant, with travelers often praising the amazing staff and spacious rooms.

If you're looking for the best value vacation packages in Windsor, the Kenora Motel, rated 8.4 out of 10, provides a comfortable stay with free WiFi, and travelers frequently highlight its affordable value and modern rooms.
Is Windsor better suited for a beach vacation or a cultural trip?
Windsor is primarily an urban destination, making a Windsor vacation ideal for cultural exploration and city attractions. The city offers a rich history and vibrant arts scene, with sites like the François Bâby House, which serves as Windsor's Community Museum, and the Art Windsor-Essex gallery.

Travelers can explore historic neighborhoods like Sandwich and Walkerville, enjoy the scenic Detroit Riverwalk, or attend events like the Windsor International Film Festival. While there are waterfront parks, the focus is on urban and cultural experiences.
Is Windsor a good choice for a family vacation package?
Windsor is a strong choice for family vacation packages, offering a variety of attractions and accommodations suitable for all ages. Families can enjoy the Adventure Bay Family Water Park, located about 1 mile from central Windsor, or explore the scenic Windsor Riverfront, also about 1 mile from the city center.

For a comfortable stay, consider properties like the 3.5-star Holiday Inn & Suites Windsor Ambassador Bridge by IHG, which offers family rooms and an indoor pool, making it a convenient base for exploring the city.
What are the top things to do in Windsor?
A Windsor vacation offers a variety of urban attractions and activities for different interests:

Browse and book things to do in Windsor on Expedia.
Do you need to rent a car in Windsor, or is public transport enough?
For a Windsor vacation package, a rental car offers the most flexibility, especially if you plan to explore beyond the downtown core. While the Transit Windsor bus system provides an inexpensive way to get around the city center, many attractions are quite spread out, and a rental car offers more convenience for reaching them.

If your Windsor vacation packages with flights arrive at Windsor International Airport (YQG) or Detroit Metropolitan Wayne County Airport (DTW), a rental car can also simplify your journey to and from your accommodation. Local taxis and ride-share apps are also available for shorter trips.
Are Windsor vacation package hotels conveniently located?
Windsor vacation package hotels offer convenient locations, with many properties situated close to the city center.

For example, TownePlace Suites by Marriott Windsor and Holiday Inn Express Windsor Waterfront by IHG are both about a 5-minute walk from central Windsor. Hampton Inn & Suites by Hilton Windsor is also well-located, about 2 miles from the city center. These central locations provide easy access to many of Windsor's attractions and amenities.
Are there vacation package hotels in Windsor within walking distance of restaurants and shops?
Central Windsor vacation package hotels place restaurants and shops within easy walking distance. The city center is home to a variety of dining and retail options, including those found in areas like Little Italy on Erie Street.

For example, TownePlace Suites by Marriott Windsor and Holiday Inn Express Windsor Waterfront by IHG are both about a 5-minute walk from central Windsor, providing convenient access to nearby amenities. When choosing your package, consider hotels in the downtown area for the best walkability.
Can I change or cancel my Windsor vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Windsor vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Windsor vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Windsor?
To find last-minute vacation packages to Windsor, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Windsor vacation packages?
Free cancellation on a Windsor vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Windsor vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Windsor getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Windsor vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.