Windsor Vacation Packages

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Your Windsor Vacation

When a city stay is calling, answer it with a Windsor vacation package. With all your travel needs in place before you leave, all you have to do here is concentrate on having fun. Every trip to Windsor should include a little sightseeing. le Parc Historique de la Poudriere de Windsor is a superb place to kick off your exploring. Your Windsor vacation is just a few clicks away. Browse airfares, hotels and more on Expedia for a trip that's tailored to suit your travel style.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Masquerade Tower at Rio Hotel & Casino

Masquerade Tower at Rio Hotel & Casino

3 out of 5
Price was CA $673, price is now CA $344 per person
CA $344
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
7.8/10 Good! (4,230 reviews)
Masquerade tower needs renovation, my rooms shower head was broken, water would come out of shower head and bath head the lever you pull up wouldn’t go up all the way, water would leak out of the cold and hot handles from sink, the wallpaper was peeling, the light bulbs in the vanity went out and stopped working , found chips under my bed , the bath tub was clogged and would take forever to drain the water , room service never came I had to go look for them, pretty bad experience but pool was fun

Reviewed on Jul 12, 2026

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Price was CA $1,460, price is now CA $732 per person
CA $732
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Los Angeles (LAX)
8.6/10 Excellent! (713 reviews)
As always the hotel is clean and quiet easy access to nearby locations

Reviewed on Jul 13, 2026

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite

4.5 out of 5
Price was CA $5,525, price is now CA $3,000 per person
CA $3,000
per person
Sep 23 - Sep 25
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Las Vegas (LAS)
8.6/10 Excellent! (4 reviews)
The view was gorgeous at night with all the lights. We loved it! ~ Always Grateful. ~

Reviewed on May 7, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $13,004, price is now CA $7,130 per person
CA $7,130
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Virgin Hotel Las Vegas, Curio Collection by Hilton

Virgin Hotel Las Vegas, Curio Collection by Hilton

4.5 out of 5
Price was CA $821, price is now CA $454 per person
CA $454
per person
Sep 20 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
9/10 Wonderful! (8,281 reviews)
It was nice and simple, staff was great

Reviewed on Jul 13, 2026

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Manoir Des Sables, an Ascend Collection Hotel

Manoir Des Sables, an Ascend Collection Hotel

4 out of 5
90 Des Jardins Ave. Orford QC
Fully refundable
The price is CA $118 per night from Aug 9 to Aug 10
CA $118
CA $149 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (1,341 reviews)
"The staff is helpful"

Reviewed on Jul 12, 2026

Manoir Des Sables, an Ascend Collection Hotel
Hotel Cheribourg, an Ascend Collection Hotel

Hotel Cheribourg, an Ascend Collection Hotel

4 out of 5
2603 Chemin Du Parc Orford QC
Fully refundable
The price is CA $113 per night from Jul 16 to Jul 17
CA $113
CA $143 total
Jul 16 - Jul 17
includes taxes & fees
8.2/10 Very good! (1,249 reviews)
"Amazing place for kids! Such a cool games room, multiple pools, petting zoo, our three kids loved it. Room could have been a bit cleaner and outside building walkway needed some fixing, but we'd definitely stay again."

Reviewed on Jul 13, 2026

Hotel Cheribourg, an Ascend Collection Hotel
OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

5 out of 5
3131 rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
The price is CA $229 per night from Jul 19 to Jul 20
CA $229
CA $273 total
Jul 19 - Jul 20
includes taxes & fees
9.8/10 Exceptional! (1,777 reviews)
"Hôtel magnifique, spas relaxant et personnel souriant !"

Reviewed on Jul 12, 2026

OTL Gouverneur Sherbrooke
See all 189 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.
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Stay near popular Windsor attractions

le Parc Historique de la Poudriere de Windsor

Find out about the history of Windsor with a stop at le Parc Historique de la Poudriere de Windsor. You can enjoy the restaurants while in the area.
See properties

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $344 on Expedia for your Windsor break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
January, February and November are great times to look for cheap Windsor vacation packages. Choosing to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Windsor?
Typically, a handful of days is enough to visit the major attractions during your Windsor vacation. However, if you prefer to have some time to relax or go on day tours, think about extending your itinerary.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling 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 cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a customized Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
Enjoy incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor trip.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to visit Windsor.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Windsor.
  3. Decide your trip length: Think about how long you want to spend discovering Windsor. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Windsor vacation package.

Explore a world of travel with Expedia

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