Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Roanoke Island Inn
Historic Downtown Manteo
CA $1,361
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
10/10 Exceptional! (100 reviews)
The property was very clean and inviting. Lee, the caretaker of the property was wonderful ! Will be back soon !!!
Reviewed on Sep 11, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Fully refundable
CA $129
CA $150 total
Oct 15 - Oct 16
includes taxes & fees
Wyndham Garden Norfolk Downtown
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
CA $129
CA $153 total
Sep 27 - Sep 28
includes taxes & fees
Kingsmill Resort
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $227
CA $325 total
Oct 4 - Oct 5
includes taxes & fees
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)
You can study the exhibits at Boykin's Tavern, a museum with a storied past, during your trip to Isle of Wight. Discover the area's live music and churches.
Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals from CA $925 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 many days is enough for Windsor?
With a well-organized itinerary, you can easily visit the most popular Windsor sights in a handful of days. But if you want to venture off the beaten track or go on day trips, consider booking your Windsor vacation for longer.
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 travelling on a whim.
How to plan a trip to Windsor?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
