Windsor Vacations from $316

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Las Vegas Hilton at Resorts World

Las Vegas Hilton at Resorts World

4.5 out of 5
Las Vegas Strip
Price was $981, price is now $316 per person
$316
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8.8/10 Excellent! (14,911 reviews)

Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Price was $1,078, price is now $410 per person
$410
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8.8/10 Excellent! (1,013 reviews)

Conrad Las Vegas at Resorts World

Conrad Las Vegas at Resorts World

5 out of 5
Las Vegas Strip
Price was $1,148, price is now $490 per person
$490
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
9/10 Wonderful! (6,228 reviews)

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $1,006, price is now $433 per person
$433
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (952 reviews)
There was a lot of very early morning noise in the halls, but other than that, there was very little to complain about! We plan to stay here again if we come back in the future!

Reviewed on Nov 13, 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was $1,214, price is now $542 per person
$542
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Great location, rooms with personality but still super clean. Staff are helpful but not pushy. Definitely looking to stay here again.

Reviewed on Nov 13, 2026

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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.
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Windsor Hotel Deals

Grand Hotel Times Sherbrooke

Grand Hotel Times Sherbrooke

4 out of 5
1, rue Belvedere Sud Sherbrooke QC
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $149 total per night from Dec 3 to Dec 4
$149 total
Dec 3 - Dec 4
Total with taxes and fees
Grand Hotel Times Sherbrooke
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
$53 nightly
The price is $62 total per night from Dec 14 to Dec 15
$62 total
Dec 14 - Dec 15
Total with taxes and fees
8.4/10 Very Good! (1,552 reviews)
"Le tapis devrait être retiré partout car il est sale. Un peu vieillot comme hôtel mais bien malgré tout"

Reviewed on Nov 12, 2026

Manoir Des Sables, an Ascend Collection Hotel
Hôtel Le Président

Hôtel Le Président

3 out of 5
3535, rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $125 total per night from Nov 15 to Nov 16
$125 total
Nov 15 - Nov 16
Total with taxes and fees
8/10 Very Good! (1,027 reviews)
"The staff was warm and welcoming. The pool was very cold for an indoor pool, but the hot tub was really enjoyable. My only complaint are the beds. The mattress was horribly uncomfortable."

Reviewed on Nov 12, 2026

Hôtel Le Président
See all 193 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

Windsor Essential Information

Language
English
Currency
Canadian dollars
Population
5,400
Top Sights
Centre dInterpretation de lArdoise, Centre dInterprétation de lHistoire de Sherbrooke and Sherbrooke Golf Club

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $316 on Expedia for your Windsor getaway. However, factors like the length of stay, hotel choice and season 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 traveling in December, January and February. You'll generally find lower prices on hotels and airfares during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
Usually, a handful of days is enough to see the top sights during your Windsor vacation. But if you prefer to have time to unwind or take day trips, think about extending your itinerary.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Windsor package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a customized Windsor vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Windsor?
If you're planning a spontaneous Windsor vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Set off on your dream trip to Windsor with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until the next payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to stick to your budget and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.