Windsor Vacation Packages

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    Better together

    Save up to CA $1,096 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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    Plan, book, and manage your trip all in one place

Windsor Hotel Deals

Lancaster Arts Hotel

Lancaster Arts Hotel

3.5 out of 5
300 Harrisburg Ave, Lancaster, PA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jul 20 to Jul 21
CA $174
CA $193 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Vibey and classy! Thoughtful provisions in the bathroom 🌻"

Reviewed on Jul. 15, 2025

Lancaster Arts Hotel
Eden Resort and Suites, BW Premier Collection

Eden Resort and Suites, BW Premier Collection

3.5 out of 5
222 Eden Road, Lancaster, PA
9/10 Wonderful! (1,000 reviews)
"Great"

Reviewed on Jul. 15, 2025

Get rates
Eden Resort and Suites, BW Premier Collection
Lancaster Marriott at Penn Square

Lancaster Marriott at Penn Square

3.5 out of 5
25 South Queen Street, Lancaster, PA
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Jul 23 to Jul 24
CA $247
CA $274 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Was such a great area and close to everything"

Reviewed on Jul. 17, 2025

Lancaster Marriott at Penn Square
See all 457 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.

Beach Vacations

Beach Vacations

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.