Windsor Vacation Packages

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    Save up to CA $1,096 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

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort
Four Sails Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Holiday Inn & Suites Virginia Beach North Beach by IHG
Coastal Hotel and Suites Virginia Beach Oceanfront

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

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 CA $186 per night from Sep 1 to Sep 2
CA $186
CA $219 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Good Hotel, so so restaurant
"Staff was friendly and efficient. I don't like the not making the room up, they missed it on day 2. But room was large, bed okay, having a desk with outlets was awesome for a road warrior. The restaurant was a different story, service was rotten. The wait staff were standing in the back behind a ..."

Reviewed on Aug. 4, 2025

Norfolk Waterside Marriott
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 CA $121 per night from Sep 1 to Sep 2
CA $121
CA $142 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (886 reviews)
"Good hotel would stay again"

Reviewed on Aug. 5, 2025

Comfort Inn & Suites Hampton near Coliseum
Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
1905 Coliseum Dr, Hampton, VA
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Sep 1 to Sep 2
CA $132
CA $154 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,256 reviews)
phenomenal family place
"it was an amazing stay very family friendly our kids had a phenomenal time"

Reviewed on Aug. 4, 2025

Hyatt Place Hampton Convention Center
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 from CA $1,374 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?

  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.

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