Windsor Vacations from $526

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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.
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was $2,474, price is now $526 per person
$526
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was $3,217, price is now $671 per person
$671
per person
Jul 17 - Jul 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
6/10 (2 reviews)
Brickell Bay 3304

Brickell Bay 3304

3 out of 5
Brickell
Price was $2,474, price is now $526 per person
$526
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
New York (NYC) to Miami (MIA)
No reviews
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was $3,395, price is now $848 per person
$848
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on Apr 14, 2026

MirabileCondoDwntown MIA Brickell w PRKG

MirabileCondoDwntown MIA Brickell w PRKG

5 out of 5
Downtown Miami
Price was $2,216, price is now $710 per person
$710
per person
Jun 12 - Jun 17
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
2/10 (2 reviews)
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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

OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

5 out of 5
3131 rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $204 total per night from May 10 to May 11
$204 total
May 10 - May 11
Total with taxes and fees
9.8/10 Exceptional! (1,741 reviews)
Always a pleasure staying here.

Reviewed on May 6, 2026

OTL Gouverneur Sherbrooke
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
$178 nightly
The price is $211 total per night from May 21 to May 22
$211 total
May 21 - May 22
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
There was no restaurant other than at breakfast and the pool was not in service

Reviewed on May 7, 2026

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
$61 nightly
The price is $72 total per night from Jun 7 to Jun 8
$72 total
Jun 7 - Jun 8
Total with taxes and fees
8.4/10 Very Good! (1,293 reviews)
Good

Reviewed on Apr 28, 2026

Manoir Des Sables, an Ascend Collection Hotel
See all 191 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 $526 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.