Windsor Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Windsor
Wyndham Garden Norfolk Downtown
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
S$133
7 Sept - 8 Sept
includes taxes & fees
Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Fully refundable
S$141
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (1,119 reviews)
"Clean"
Reviewed on 24 Aug, 2026
Kingsmill Resort
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
S$332
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,026 reviews)
"The resort was nice and the amenities were great. Nice river pool with lazy river and the pool at the fitness center was nice. The one bedroom condo was spacious and clean albeit the living area a bit dark. My only complaint is that there were spider webs everywhere. There doesn’t appear to be much ..."
Reviewed on 24 Aug, 2026
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.
Stay near popular Windsor attractions
Boykin's Tavern
8.0/10 (1 review)
This 18th-century tavern showcases original colonial panelling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.
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?
- 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.
- 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.
- 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.
- 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.
