Windsor Vacation Packages

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Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
per person
Sep 9 - Sep 16
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.8/10 Good! (1,400 reviews)
Fantastic, very professional

Reviewed on Aug. 2, 2025

Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
per person
Sep 9 - Sep 16
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.6/10 Good! (36 reviews)
Great balcony with a great view

Reviewed on Aug. 2, 2025

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 out of 5
Northeast Virginia Beach
per person
Sep 9 - Sep 16
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.2/10 Very Good! (1,108 reviews)
Good location, everything was close by walking distance

Reviewed on Aug. 7, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Northeast Virginia Beach
per person
Sep 9 - Sep 16
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.8/10 Good! (1,015 reviews)
We stayed at this property six years ago and then recently in August 2025. It’s a great location, near the king Neptune statue. Very quiet on the north end of the strip, which is why we stay there. The downfall of this property is the condition. They haven’t done any renovations since we were there last so I hope that’s in the future for this place. The pool is nice. The outdoor bar is good enough for lunch. Drinks are a little expensive but everything in Virginia Beach is like that. I don’t like that we had to pay for parking, which is normally free at every Holiday Inn. The beds are comfortable. Overall, we had a good day.

Reviewed on Aug. 7, 2025

Coastal Hotel and Suites Virginia Beach Oceanfront

Coastal Hotel and Suites Virginia Beach Oceanfront

2.5 out of 5
Northeast Virginia Beach
per person
Sep 9 - Sep 16
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
9.2/10 Wonderful! (1,205 reviews)
Nice breakfast, excellent location and friendly staff made our stay fantastic.

Reviewed on Aug. 5, 2025

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
See all 689 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.
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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.