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.
Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

Spring Valley
CA $538
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
8.8/10 Excellent! (1,009 reviews)
The place is nice. The staff was very friendly and helpful. The only issue I had was the bedroom tv would not turn off. I had to unplug it. It was quiet and relaxing. It is close enough to the strip if you want hit a casino or a show, and you don’t have to deal with the loud noise. It was a little weird to have the bath tub in the bedroom. But for couples that could be a plus.

Reviewed on Aug 20, 2026

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

South of Wilshire
CA $818
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.2/10 Very good! (1,012 reviews)
Our overall experience was disappointing, particularly when it came to service and attention to detail. The hotel did not seem to be on top of basic room maintenance. For example, the closet door in our room would not open properly—something that should have been noticed and corrected before a guest checked in. We also found the front desk staff to be unnecessarily rigid and felt that the hotel nickel-and-dimed its guests. Our room was already cleaned and available when we arrived around noon, yet we were told we would have to pay an additional $50 if we wanted to check in before 2:00 PM. I can understand an early check-in fee when special arrangements are required, but charging $50 when the room was already sitting ready seemed excessive. On the way to our room, we noticed another room in the same price category that appealed to us a little more. We politely asked if we could switch to that room and were given a flat “No,” without any explanation or attempt to accommodate us. Finally, a large yellow “Wet Floor” sign was left directly in front of our room for our entire two-night stay. When we asked if it could be moved, we were simply told that it could not. It may seem like a small issue, but it was another example of the lack of attention and flexibility we experienced throughout our stay. Our impression of the hotel is that could benefit greatly from better attention to its rooms and a more accommodating, guest-friendly approach to service.

Reviewed on Aug 26, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $14,517
per person
Oct 28 - Nov 3
found 10 hours 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

Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

CA $1,274
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.4/10 Very good! (1,989 reviews)
One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite- NO RESORT FEE

One Bedroom | 1.5 Baths & Living Room | Jet Tub – Palms Place StripSuite- NO RESORT FEE

CA $1,902
per person
Nov 14 - Nov 20
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) 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

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

90 Des Jardins Ave. Orford QC
Fully refundable
CA $114
CA $144 total
Sep 21 - Sep 22
includes taxes & fees
8.4/10 Very good! (1,419 reviews)
"Les draps étaient mal installés"

Reviewed on Aug 26, 2026

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

Hotel Cheribourg, an Ascend Collection Hotel

2603 Chemin Du Parc Orford QC
Fully refundable
CA $101
CA $129 total
Sep 20 - Sep 21
includes taxes & fees
Hotel Cheribourg, an Ascend Collection Hotel
OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

3131 rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
CA $227
CA $270 total
Sep 27 - Sep 28
includes taxes & fees
OTL Gouverneur Sherbrooke
See all 192 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.

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 $538 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.