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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    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Windsor

Kingsmill Resort
Kingsmill Resort
4 out of 5
1010 Kingsmill Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is S$270 per night from 1 Jan to 2 Jan
S$270
includes taxes & fees
1 Jan - 2 Jan,2025
8.8/10 Excellent! (1,005 reviews)
"if you are looking for quiet,upscale,and to relax this is your place."

Reviewed on 27 Nov,2024

Kingsmill Resort
Comfort Inn Newport News - Hampton I-64
Comfort Inn Newport News - Hampton I-64
2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 17 Dec to 18 Dec
S$115
includes taxes & fees
17 Dec - 18 Dec
8.4/10 Very Good! (1,003 reviews)
"Everything was fantastic, I'm going back tonight in fact"

Reviewed on 30 Nov,2024

Comfort Inn Newport News - Hampton I-64
Courtyard by Marriott Norfolk Downtown
Courtyard by Marriott Norfolk Downtown
3 out of 5
520 Plume street, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 8 Dec to 9 Dec
S$134
includes taxes & fees
8 Dec - 9 Dec
8/10 Very Good! (1,002 reviews)
"The room was on the small side, but it was creatively and efficiently laid out. The bed was fairly comfortable. The shower MAY have been the best shower head/water pressure I've ever used."

Reviewed on 26 Nov,2024

Courtyard by Marriott Norfolk Downtown
See all 697 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?
Starting from as low as , a package is your ticket to low-cost travel. Custom make your Windsor getaway by picking from our great range of flights, hotels and rental cars.
How do I get a cheap travel package to Windsor?
Just think of all the thrilling things you could do in Windsor with extra cash in your pocket. Watch your savings stack up when you bundle your hotel and flights into a Windsor holiday package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 properties globally. Whether you’re heading off with the family or travelling on your own, planning a trip to Windsor is better with a package.
How far in advance should I book my Windsor holiday?
To land cheap prices, book as soon as you can. Air carriers typically advertise flight tickets, along with some of the lowest fares, around 12 months in advance. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you’re in need of a last-minute getaway to Windsor, there are always lots of great bargains to be had on Expedia. Check them out now!
What does an Expedia Windsor travel package include?
That depends on you. You can pick from a range of Windsor packages, such as a rental car, flight and hotel. You can also book a hotel with a flight, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like activities and experiences. Whatever your Windsor trip looks like, get ready to save!
What should I know before booking a Windsor travel package?
So many places to wander around, so many things to do. With a travel package, you’ll be able to tick more of them off your list. Combine your hotels, flights and rental cars and get set to save.
Can I choose my airline with a Windsor Expedia holiday package?
Yes, and with over 550 airlines to choose from around the world, you have loads of choice. Have a look through the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Windsor holiday package?
Whether it’s your hotel or flight, you can cancel or amend it. Booked your Windsor holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may be charged a fee by your hotel, airline or car rental company. For more information, browse our Customer Service Portal. We’re here to help you each step of the way.

* 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.