Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ₩234,741 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

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Hyatt Place Hampton Convention Center
Hyatt Place Hampton Convention Center
3 out of 5
1905 Coliseum Dr, Hampton, VA
The price is ₩142,530 per night from Jun 30 to Jul 1
₩142,530
₩166,651 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,230 reviews)
"We will return. The staff was great."

Reviewed on Jun 23, 2025

Hyatt Place Hampton Convention Center
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 ₩186,481 per night from Jul 1 to Jul 2
₩186,481
₩218,597 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"Nice hotel if you want to stay near the water downtown"

Reviewed on Jun 21, 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 ₩150,273 per night from Jul 7 to Jul 8
₩150,273
₩175,553 total
Jul 7 - Jul 8
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"It’s was great"

Reviewed on Jun 20, 2025

The Landing at Hampton Marina, Tapestry Collection by Hilton
See all 674 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 vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation packages and you could score some excellent off-season deals.
How many days is enough for Windsor?
With a well-organized 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 vacation 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 vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a tailored vacation 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 vacation 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 personalized Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.