Windsor Vacations from $207

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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.
Paris Las Vegas Resort & Casino

Paris Las Vegas Resort & Casino

4 out of 5
Las Vegas Strip
Price was $650, price is now $207 per person
$207
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8/10 Very Good! (24,028 reviews)
Really liked the hotel!

Reviewed on Oct 1, 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
Price was $37,781, price is now $17,682 per person
$17,682
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1 review)
Beach Place Hotel

Beach Place Hotel

2 out of 5
North Beach
Price was $957, price is now $460 per person
$460
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1,002 reviews)
Close to the beach and park

Reviewed on Sep 2, 2025

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
Price was $617, price is now $315 per person
$315
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.6/10 Excellent! (209 reviews)
Well maintained property, comfy bed, easy parking and convenient location. Should consider adding a microwave and coffee/tea maker.

Reviewed on Oct 1, 2025

Fleur Noire Hotel - 21 and Over

Fleur Noire Hotel - 21 and Over

3.5 out of 5
Uptown Design District
Price was $1,028, price is now $527 per person
$527
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
9.6/10 Exceptional! (824 reviews)
Great set up. All rooms are pretty much pool side. Staff were super friendly/helpful.

Reviewed on Sep 28, 2025

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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

Windsor Hotel Deals

Hôtel Le Président

Hôtel Le Président

3 out of 5
3535, rue King Ouest, Sherbrooke, QC
$108 nightly
The price is $128 total per night from Oct 5 to Oct 6
$128 total
Oct 5 - Oct 6
Total with taxes and fees
8/10 Very Good! (1,034 reviews)
"Good"

Reviewed on Sep 30, 2025

Hôtel Le Président
Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

4 out of 5
90 Des Jardins Ave., Orford, QC
$72 nightly
The price is $86 total per night from Oct 2 to Oct 3
$86 total
Oct 2 - Oct 3
Total with taxes and fees
8.2/10 Very Good! (1,119 reviews)
"Clean property, friendly staff"

Reviewed on Sep 20, 2025

Manoir des Sables Hôtel & Golf
OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

5 out of 5
3131 rue King Ouest, Sherbrooke, QC
$161 nightly
The price is $192 total per night from Oct 26 to Oct 27
$192 total
Oct 26 - Oct 27
Total with taxes and fees
9.6/10 Exceptional! (1,582 reviews)
"Excellent service, excellent breakfast. Staff couldn’t be nicer. Beautiful room, hotel, and facilities. Enjoyed the hot tub and the indoor pool."

Reviewed on Sep 30, 2025

OTL Gouverneur Sherbrooke
See all 172 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.

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 $207 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.