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.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.6/10 Excellent! (115 reviews)
Clean, quiet, newly renovated, easy & convenient parking, very reasonable rate on a Monday night.

Reviewed on Aug. 6, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Oct 12 - Oct 17
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1 review)
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.4/10 Very Good! (2,650 reviews)
The location is excellent, and it is a clean and quiet place.

Reviewed on Aug. 9, 2025

The Cole

The Cole

3.5 out of 5
Little Tuscany
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.4/10 Very Good! (291 reviews)
charge for parking no shade in pool area

Reviewed on Jun. 17, 2025

Carlyle Inn

Carlyle Inn

3.5 out of 5
Pico - Robertson
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8/10 Very Good! (948 reviews)
I prefer a local boutique neighborhood hotel to a chain, and The Carlyle Inn delivers that experience. The Robertson-Pico neighborhood is a lively area of LA bordering on Beverly Hills. A well-maintained property overall, the room was spotlessly clean, and the king bed very comfortable. The front desk is staffed 24 hours a day. I received free self-parking as a VIP bonus. Tip: use the bath mat when showering; the tub was very slippery.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 1 to Sep 2
CA $106
CA $127 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,034 reviews)
Great experience
"Staff was amazing and very helpful in any questions always smiling. The buffet was great ! The activity around the hotel was wonderful with the children!"

Reviewed on Aug. 6, 2025

Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke

Grand Times Hotel Sherbrooke

4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundableReserve now, pay when you stay
The price is CA $216 per night from Aug 11 to Aug 12
CA $216
CA $257 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"We enjoyed the entire stay. This bed was wonderful! The staff so helpful and friendly as we were from America. We were able to walk to our place for dinner and sat and enjoyed the sights. Beautiful hotel!"

Reviewed on Aug. 7, 2025

Grand Times Hotel Sherbrooke
Hôtel Chéribourg

Hôtel Chéribourg

4 out of 5
2603 Chemin Du Parc, Orford, QC
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Aug 24 to Aug 25
CA $110
CA $139 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,195 reviews)
"Super spot. Had a fantastic stay. Unfortunately restaurant is closed on Monday’s so we were unable to try any food."

Reviewed on Aug. 6, 2025

Hôtel Chéribourg
See all 175 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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Discover the most popular places to visit in Windsor

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.

le Parc Historique de la Poudriere de Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $566 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.

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