Windsor Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top hotels in Windsor

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 S$258 per night from 13 Jul to 14 Jul
S$258
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,038 reviews)
"Wonderful stay second time visiting in the summer . The property is very clean and housekeeping does a wonderful job with the clean rooms which is makes for a relaxing vacation . Everyone is so friendly . The resort is an amazing especially for families . The amenities are wonderful to keep them ..."

Reviewed on 3 Jul, 2026

Eden Resort and Suites, BW Premier Collection
SureStay Plus by Best Western Elizabethtown Lancaster

SureStay Plus by Best Western Elizabethtown Lancaster

2.5 out of 5
147 Merts Drive Elizabethtown PA
Fully refundableReserve now, pay when you stay
The price is S$140 per night from 13 Jul to 14 Jul
S$140
13 Jul - 14 Jul
includes taxes & fees
8.8/10 Excellent! (997 reviews)
"It’s good but not great. It ok for price"

Reviewed on 1 Jul, 2026

SureStay Plus by Best Western Elizabethtown Lancaster
Cork Factory Hotel Lancaster

Cork Factory Hotel Lancaster

3 out of 5
480 New Holland Avenue Suite 3000 Lancaster PA
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 21 Jul to 22 Jul
S$185
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Very well kept hotel and the staff was helpful with any questions we had about the area"

Reviewed on 2 Jul, 2026

Cork Factory Hotel Lancaster
See all 506 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.

Explore a world of travel with Expedia

* 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.