Windsor Vacations from $231

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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.
Harrah’s Las Vegas – A Caesars Rewards Destination

Harrah’s Las Vegas – A Caesars Rewards Destination

3.5 out of 5
Las Vegas Strip
Price was $709, price is now $231 per person
$231
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
15.6/10 Exceptional! (13,765 reviews)
Clean room. Middle of the strip

Reviewed on Nov 16, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,122, price is now $870 per person
$870
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
19.2/10 Exceptional! (53 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on Nov 16, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $1,291, price is now $531 per person
$531
per person
Jan 16 - Jan 23
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to New York (NYC)
18.4/10 Exceptional! (2,007 reviews)
Great room and polite staff and excellent restaurant and location.

Reviewed on Nov 15, 2025

The LINQ Hotel & Casino – A Caesars Rewards Destination

The LINQ Hotel & Casino – A Caesars Rewards Destination

4 out of 5
Las Vegas Strip
Save 100% on your flight
Price was $677, price is now $281 per person
$281
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
15.6/10 Exceptional! (17,624 reviews)
Room: restroom no fan, so weird Hotel front door: the water pipes broke, too much water , hard to pick up

Reviewed on Nov 16, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $5,298, price is now $2,285 per person
$2,285
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
16/10 Exceptional! (1,004 reviews)
Enjoyed a few days with the kids gere

Reviewed on Nov 15, 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

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
$143 nightly
The price is $171 total per night from Dec 1 to Dec 2
$171 total
Dec 1 - Dec 2
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
.

Reviewed on Nov 12, 2025

Grand Times Hotel Sherbrooke
Manoir des Sables Hôtel & Golf

Manoir des Sables Hôtel & Golf

4 out of 5
90 Des Jardins Ave. Orford QC
Fully refundable
$67 nightly
The price is $79 total per night from Nov 17 to Nov 18
$79 total
Nov 17 - Nov 18
Total with taxes and fees
8.2/10 Very Good! (1,159 reviews)
Very clean, quiet and spacious room; comfortable beds; very safe place and area; breakfast had great options for vegetarians. Overall, would recommend it to my friends and will stay again myself.

Reviewed on Nov 5, 2025

Manoir des Sables Hôtel & Golf
OTL Gouverneur Sherbrooke

OTL Gouverneur Sherbrooke

5 out of 5
3131 rue King Ouest Sherbrooke QC
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $182 total per night from Nov 30 to Dec 1
$182 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (1,603 reviews)
Very nice

Reviewed on Nov 12, 2025

OTL Gouverneur Sherbrooke
See all 178 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 $231 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.