Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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.
Miracle Motel

Miracle Motel

2.5 out of 5
Harwich
per person
Aug 19 - Aug 25
found 2 hours ago
Roundtrip flight included
Calgary (YYC) to Windsor (YQG)
8.6/10 Excellent! (39 reviews)
Classic motel recently updated. Spartan, but clean.

Reviewed on Jun. 5, 2025

Windsor Manor

Windsor Manor

4 out of 5
City Centre
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Comox (YQQ) to Windsor (YQG)
No reviews
Super 8 by Wyndham Ambassador Bridge Windsor ON

Super 8 by Wyndham Ambassador Bridge Windsor ON

2 out of 5
Sandwich
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Comox (YQQ) to Windsor (YQG)
7.6/10 Good! (1,005 reviews)
Ckean rooms but aweful outside appearance

Reviewed on Jul. 6, 2025

Super 8 by Wyndham Windsor/Dougall

Super 8 by Wyndham Windsor/Dougall

2 out of 5
Remington Park
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Comox (YQQ) to Windsor (YQG)
7.8/10 Good! (1,003 reviews)
Breakfast was terrible and they ran out of cups

Reviewed on Jul. 9, 2025

Caesars Windsor

Caesars Windsor

4 out of 5
City Centre
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Comox (YQQ) to Windsor (YQG)
8.6/10 Excellent! (2,993 reviews)
We appreciated the level of security at the property.

Reviewed on Jul. 11, 2025

Where to stay in Windsor

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

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 Chrysler Theatre are top sights worth seeing.

Find hotels in Downtown Windsor

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 $136 per night from Jul 20 to Jul 21
CA $136
CA $163 total
Jul 20 - Jul 21
includes taxes & fees
8/10 Very Good! (1,005 reviews)
"Great value. Staff was excellent considering the labor dispute ongoing. We were given a room with a very nice view and watched distant fireworks shows until midnight"

Reviewed on Jul. 10, 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 Jul 13 to Jul 14
CA $152
CA $207 total
Jul 13 - Jul 14
includes taxes & fees
8.4/10 Very Good! (3,012 reviews)
"This place is always my first choice now no questions asked"

Reviewed on Jul. 9, 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 Jul 20 to Jul 21
CA $165
CA $198 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Great hotel and service.
"Great room and service. Parking garage attached to the hotel was convenient. We had a view of the riverwalk parkway and the Detroit skyline. Hotel was clean and quiet."

Reviewed on Jul. 8, 2025

DoubleTree by Hilton Windsor Hotel & Suites
See all 361 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Windsor

Caesars Casino

Caesars Casino

4.5/5(93 reviews)

Why not try your luck with a visit to Caesars Casino during your time in Windsor? Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.

Caesars Casino
Ambassador Bridge

Ambassador Bridge

1.5/5(3 reviews)

You can learn about the history of Windsor with a visit to Ambassador Bridge. Stroll along the riverfront or experience the entertainment choices in this vibrant area.

Ambassador Bridge
Willistead Manor

Willistead Manor

You can learn about the history of Windsor when you stop by Willistead Manor. Stroll along the riverfront or visit the casinos in this vibrant area.

Willistead Manor

What to do in Windsor

Step into the shadows and discover the haunting tales of Motor City's past.

Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour

CA $44
per adult
Motor City Ghosts: Haunts, Spirits, and Poltergeists Walking Tour
Explore Michigan Private Half-Day Walking Tour

Best Downtown Detroit Historical Walking Tour

CA $144
per adult
Best Downtown Detroit Historical Walking Tour
Detroit: Architectural Beauty and Hidden Gems Walking Tour

Detroit: Architectural Beauty and Hidden Gems Walking Tour

CA $185
per adult
Detroit: Architectural Beauty and Hidden Gems Walking Tour
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $654 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.