Windsor Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Windsor Vacation

The adventure-filled city of Windsor is calling. Discover its highlights and hidden gems with a Windsor vacation package that's tailored to you. If some sightseeing is on your list of things to do during your trip to Windsor, swing by well-known attractions like Aiken State Park. Whoever you're escaping with and whatever you plan to spend, your ultimate Windsor vacation is just a few clicks away with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Grovetown Augusta

Baymont by Wyndham Grovetown Augusta

2.5 out of 5
Price was CA $1,032, price is now CA $1,032 per person
CA $1,032
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AGS)
8.8/10 Excellent! (1,001 reviews)

Hyatt House Augusta Downtown

Hyatt House Augusta Downtown

3.5 out of 5
Downtown Augusta
Price was CA $1,166, price is now CA $1,131 per person
CA $1,131
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AGS)
9/10 Wonderful! (1,002 reviews)

Hyatt Place Augusta

Hyatt Place Augusta

3 out of 5
Price was CA $1,124, price is now CA $1,092 per person
CA $1,092
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AGS)
8.6/10 Excellent! (1,000 reviews)

Hampton Inn & Suites by Hilton Augusta-Washington Rd

Hampton Inn & Suites by Hilton Augusta-Washington Rd

2.5 out of 5
Montclair
Price was CA $1,070, price is now CA $1,053 per person
CA $1,053
per person
Jan 1 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AGS)
8.8/10 Excellent! (1,121 reviews)
Friendly and welcoming staff, room was fresh and clean.

Reviewed on Nov 10, 2026

Hampton Inn Waynesboro

Hampton Inn Waynesboro

2.5 out of 5
Price was CA $1,532, price is now CA $1,510 per person
CA $1,510
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AGS)
8.8/10 Excellent! (401 reviews)
Nice place to stay with family for a weekend

Reviewed on Nov 8, 2026

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Aiken Midtown Hotel

Aiken Midtown Hotel

2.5 out of 5
100 Tamil Dr Aiken SC
The price is CA $112 per night from Nov 24 to Nov 25
CA $112
CA $125 total
Nov 24 - Nov 25
includes taxes & fees
Aiken Midtown Hotel
Country Inn & Suites by Radisson, Aiken South

Country Inn & Suites by Radisson, Aiken South

2.5 out of 5
3270 Whiskey Rd Aiken SC
Fully refundable
The price is CA $110 per night from Dec 10 to Dec 11
CA $110
CA $130 total
Dec 10 - Dec 11
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Room was very clean, spacious and had everything you would expect. The breakfast was excellent...it had everything you could think of including sausage, eggs and fried potato's which is my go to. Very friendly staff. For the price this was outstanding."

Reviewed on Nov 9, 2026

Country Inn & Suites by Radisson, Aiken South
Carriage House Inn

Carriage House Inn

3 out of 5
139 Laurens Street, Northwest  Aiken SC
Fully refundable
The price is CA $266 per night from Nov 14 to Nov 15
CA $266
CA $297 total
Nov 14 - Nov 15
includes taxes & fees
9.6/10 Exceptional! (603 reviews)
"Really lovely inn and close to everything downtown! We enjoyed our stay"

Reviewed on Nov 10, 2026

Carriage House Inn
See all 364 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.
All Inclusive Vacations
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Stay near popular Windsor attractions

Aiken State Park

You can take time to visit Aiken State Park during your travels to Windsor.
See properties

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,032 on Expedia. But how much your vacation to Windsor costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Windsor?
You're likely to find lower prices and better availability in January, February and November. Explore our cheap Windsor vacation packages and you could get some great off-season discounts.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the major sights during your Windsor vacation. But if you want to have time to chill out or go on 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 preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Windsor package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor escape off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your schedule and pack your bags. Your favourite time of year and the activities available will also help you decide when to vacation in Windsor.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can work out the ideal length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your accommodations and airfare: After you've nailed down your dates and duration, book the ideal Windsor vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.