Windsor Vacations from $179

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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.
Horseshoe Las Vegas

Horseshoe Las Vegas

4 out of 5
Las Vegas Strip
Save 100% on your flight
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.8/10 Good! (10,480 reviews)
Great location, large rooms and has a monorail stop, making it easy to get from one end of the strip to the other.

Reviewed on Aug 16, 2025

Caesars Palace

Caesars Palace

4.5 out of 5
Las Vegas Strip
per person
Sep 21 - Sep 24
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
7.8/10 Good! (12,814 reviews)
This place is amazing! A couple small critiques- no luggage rack in the room and no fridge for personal items…just items for purchase.

Reviewed on Aug 16, 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.4/10 Very Good! (1,002 reviews)
Clean hotel with great service. The only downsides to this property is that the $150 deposit wasn’t disclosed until after I already booked and prepaid for the room & the parking is $40 a night (in a garage that’s across the street). Other than that, this is a great place to spend a night or two.

Reviewed on Aug 9, 2025

Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
West Athens
per person
Oct 28 - Nov 1
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.2/10 Very Good! (1,510 reviews)
The reception lady at my date of check-in at approx after 1800.. was really personable and helpful. Excellent customer service.

Reviewed on Aug 15, 2025

Fairmont Miramar Bungalows

Fairmont Miramar Bungalows

5 out of 5
Wilshire Montana
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Los Angeles (LAX)
7.4/10 Good! (11 reviews)
My son and I enjoyed our trip very much! What a beautiful and private space.

Reviewed on Jun 6, 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

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
$57 nightly
The price is $68 total per night from Aug 25 to Aug 26
$68 total
Aug 25 - Aug 26
Total includes taxes and fees
8.2/10 Very Good! (1,055 reviews)
Rapport qualité prix excellent
"Hotel un peu vieillot, mais excellent quand même. Nous y retournerons. Les chambres sont spacieuses. Piscines et spas très agréables. Très belle situation, calme. Très bon déjeuner. Personnel professionnel, sympathique et efficace."

Reviewed on Aug 12, 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
$178 nightly
The price is $212 total per night from Aug 17 to Aug 18
$212 total
Aug 17 - Aug 18
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"I’ve had a great stay this week, was at a sports competition in Shearbrook. Hotel was excellent."

Reviewed on Aug 12, 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
8/10 Very Good! (1,199 reviews)
"Très agréable comme hôtel. Bien pour une famille."

Reviewed on Aug 12, 2025

Get rates
Hôtel Chéribourg
See all 176 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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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $179 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.