Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Eden Resort and Suites, BW Premier Collection
222 Eden Road Lancaster PA
Fully refundableReserve now, pay when you stay
CA $207
CA $230 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (1,131 reviews)
"Love, love love to staying here again 💕"
Reviewed on Sep 5, 2026
Lancaster Marriott at Penn Square
25 South Queen Street Lancaster PA
CA $261
CA $289 total
Sep 21 - Sep 22
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Awesome location. Plough is an amazing restaurant. Front desk staff highly responsive. Will come back again!"
Reviewed on Sep 4, 2026
Days Inn & Suites by Wyndham Lancaster Amish Country
2929 Hempland Rd Lancaster PA
Fully refundableReserve now, pay when you stay
CA $99
CA $110 total
Sep 7 - Sep 8
includes taxes & fees
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.
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?
- 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.
- 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.
- 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.
- 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.
