Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Windsor Vacation Packages

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 ￥18,728 per night from Jul 20 to Jul 21
￥18,728
￥20,788 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,004 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
The price is ￥31,045 per night from Jul 24 to Jul 25
￥31,045
￥34,459 total
Jul 24 - Jul 25
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Great"

Reviewed on Jul 15, 2025

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 ￥26,550 per night from Jul 23 to Jul 24
￥26,550
￥29,470 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Near the market!"

Reviewed on Jul 10, 2025

Lancaster Marriott at Penn Square
See all 454 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.

Frequently asked questions

How much does a Windsor vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Windsor costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Windsor?
January, February and March are great times to search for cheap Windsor vacation packages. Opting to travel in quieter periods means you can generally find lower prices on flights and hotels.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the top sights during your Windsor vacation. But if you prefer to have some time to unwind or go on day trips, think about extending your trip.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windsor package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor escape underway.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Windsor getaway.
How to plan a trip to Windsor?

  1. Pick your travel dates: The things you want to do in Windsor and your favorite season can help you decide when to go.
  2. Set a budget: Consider costs like food, flights and transportation when calculating how much to save for your trip to Windsor. Then, choose a property that matches your budget, whether that's a low-cost stay or a high-end getaway.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to experience in Windsor. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Windsor vacation package.

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