Windsor Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Windsor

Lancaster Arts Hotel

Lancaster Arts Hotel

3.5 out of 5
300 Harrisburg Ave, Lancaster, PA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,002 reviews)
"Good restaurant and bar. Can’t ask for a more comfortable bed and pillows"

Reviewed on 4 Aug, 2025

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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 S$243 per night from 27 Aug to 28 Aug
S$243
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Always love staying here!!!"

Reviewed on 5 Aug, 2025

Eden Resort and Suites, BW Premier Collection
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 S$102 per night from 1 Sept to 2 Sept
S$102
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Fast, friendly service, & affordable"

Reviewed on 31 Jul, 2025

Days Inn & Suites by Wyndham Lancaster Amish Country
See all 455 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Windsor costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Windsor?
January, February and March are great times to search for cheap Windsor holiday 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 holiday. 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 holiday as a package?
You can enjoy significant savings on your next Windsor break by booking a customised holiday package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday 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 favourite 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 personalised Windsor holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.