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

Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is S$217 per night from 4 Aug to 5 Aug
S$217
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"Clean facility across the street from a mall with a movie theater, Dave and Busters and plenty of dining options."

Reviewed on 12 Jul, 2025

Norfolk Waterside Marriott
The Landing at Hampton Marina, Tapestry Collection by Hilton

The Landing at Hampton Marina, Tapestry Collection by Hilton

3.5 out of 5
700 Settlers Landing Rd., Hampton, VA
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 3 Aug to 4 Aug
S$165
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (1,027 reviews)
"Not at this time"

Reviewed on 13 Jul, 2025

The Landing at Hampton Marina, Tapestry Collection by Hilton
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 20 Jul to 21 Jul
S$152
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (847 reviews)
"Everything was amazing!!"

Reviewed on 13 Jul, 2025

Comfort Inn & Suites Hampton near Coliseum
See all 684 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 great value package deals on Expedia, you'll be thrilled with how little a holiday to Windsor costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
You can typically find lower prices and better availability in January, February and November. Explore our cheap Windsor holiday packages and you could score some excellent off-season deals.
How many days is enough for Windsor?
With a well-organised itinerary, you can easily visit the main Windsor attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Windsor holiday for longer.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Windsor package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your Windsor retreat by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Windsor?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Windsor trip.
How to plan a trip to Windsor?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the type of activities on offer will also help you decide when to escape to Windsor.
  2. Budget wisely: Besides the cost of your hotel, you should consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Windsor.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels 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.