Windsor Vacation Packages

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  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Your Windsor Vacation

Book a Windsor vacation package and get set to experience this captivating city the stress-free way. Think about staying in the neighborhood of East York, which is great for shopping and history. Heritage Hill Golf Course, AvalancheXpress and Samuel S. Lewis State Park are just a few of the attractions worth visiting during your trip to Windsor. Whoever you're heading away with and whatever you want to spend, your dream Windsor vacation is just a few clicks away with Expedia.

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Windsor Hotel Deals

Eden Resort and Suites, BW Premier Collection

Eden Resort and Suites, BW Premier Collection

3.5 out of 5
222 Eden Road Lancaster PA
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Aug 13 to Aug 14
CA $253
CA $281 total
Aug 13 - Aug 14
includes taxes & fees
Eden Resort and Suites, BW Premier Collection
Cork Factory Hotel Lancaster

Cork Factory Hotel Lancaster

3 out of 5
480 New Holland Avenue Suite 3000 Lancaster PA
The price is CA $181 per night from Jul 29 to Jul 30
CA $181
CA $201 total
Jul 29 - Jul 30
includes taxes & fees
Cork Factory Hotel Lancaster
Days Inn & Suites by Wyndham Lancaster Amish Country

Days Inn & Suites by Wyndham Lancaster Amish Country

2.5 out of 5
2929 Hempland Rd Lancaster PA
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 22 to Jul 23
CA $112
CA $125 total
Jul 22 - Jul 23
includes taxes & fees
7.8/10 Good! (1,257 reviews)
"When we got there the front staff guy was very rude, whe had rented 3 rooms, the first room when we went to the bathroom there was poop on the wall and cockroaches we called front desk and he said he couldn't help up us and that there were no other rooms available and that he did not have access ..."

Reviewed on Jul 21, 2026

Days Inn & Suites by Wyndham Lancaster Amish Country
See all 513 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 on Expedia for your Windsor escape. 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 travelling in January, February and March. You're likely to find lower rates on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Windsor?
Windsor vacations can be short or long, but to really get a feel for this destination, we'd suggest 2 days is a good ballpark. This will mean you can fit in top attractions like Shank's Mare and AvalancheXpress along with lesser-known spots. Don't skip cool neighbourhoods such as Stonybrook-Wilshire and Spry either. If you're clever with your time, you may even be able to take a day trip from Windsor too.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Windsor package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Windsor?
If you've got your Windsor vacation dates confirmed, book early to score some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Windsor?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Windsor.
  2. Set your budget: Factor in costs such as transportation, flights and meals when calculating how much to put aside for your trip to Windsor. Then, choose a property that works with your budget, whether that's an economical option or a more luxurious retreat.
  3. Decide your trip length: Think about how long you'd like to spend exploring Windsor. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in 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.