Windsor Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    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

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Fully refundable
The price is SARĀ 410 per night from Jul 26 to Jul 27
SARĀ 410
SARĀ 479 total
26 Jul - 27 Jul
includes taxes & fees
Comfort Suites Airport
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 368 per night from Aug 2 to Aug 3
SARĀ 368
SARĀ 446 total
2 Aug - 3 Aug
includes taxes & fees
7/10 Good! (1,011 reviews)
"Everything was great. They allowed me to check in early which was amazing! The only negative was my tv didnā€™t work."

Reviewed on 17 July 2026

Wyndham Garden Norfolk Downtown
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 760 per night from Aug 2 to Aug 3
SARĀ 760
SARĀ 1,050 total
2 Aug - 3 Aug
includes taxes & fees
Kingsmill Resort
See all 714 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.

Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)
This 18th-century tavern showcases original colonial paneling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.
See properties

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! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Windsor vacation packages and you could get some great off-season deals.
How to find the best Windsor package deals?
Use Expedia's handy filters to find some tempting Windsor package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Windsor package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights individually. Better still, you can customize your Windsor trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor vacation dates finalized, book as early as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Windsor?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Windsor.
  2. Set your budget: Consider costs such as transportation, flights and meals when calculating how much to set aside for your trip to Windsor. Then, pick a property that suits your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Work out your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Windsor vacation package that brings all your bookings together.