
Windsor Vacation Packages
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Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Sea Ranch Resort
Price was CA $1,746, price is now CA $1,380 per person
CA $1,380
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (1,010 reviews)
Enjoyed the friendly and helpful staff. Breakfast at the restaurant was delicious.
Reviewed on Jun 22, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Northeast Virginia Beach
Price was CA $2,719, price is now CA $2,161 per person
CA $2,161
per person
Aug 8 - Aug 15
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.2/10 Very good! (1,296 reviews)
The location was great, however, it seems like an older building so the elevator took very long. The AC in the living room was extremely loud, shower head had a leak, curtain stained, and our feet were dirty instantly after a shower.
Reviewed on Jun 22, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG
Northeast Virginia Beach
Price was CA $2,687, price is now CA $2,162 per person
CA $2,162
per person
Aug 8 - Aug 15
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8/10 Very good! (1,379 reviews)
Great hotel and location. No need to drive much.
Reviewed on Jun 22, 2026

The Ocean Key Virginia Beach Resort
Northeast Virginia Beach
Price was CA $1,719, price is now CA $1,410 per person
CA $1,410
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.6/10 Good! (1,526 reviews)
This was my second stay here for the Point Break Festival and the experience was very similar. It is an older property, showing its age in places but fairly well maintained. The room was clean, comfortable and set up well. The primary issue I’ve encountered both times is the delay initially checking in because they seem to lack the staff to meet the 4 pm check in time. For 2 years I got there early but did not get into the room until after 6:30. The staff was as nice as they could be about it but nothing more than an apology is offered. Many others are in a similar situation on a Friday which seems to be a high turnover day.
Reviewed on Jun 23, 2026

Outer Banks Beach Club
Price was CA $2,087, price is now CA $1,720 per person
CA $1,720
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.8/10 Excellent! (76 reviews)
The space was very clean and seemed well maintained. There was easy access to the beach as well as having an outdoor and indoor pool. The location was great too, near lots of activities so there is always something to do!
Reviewed on Jun 18, 2026
Windsor Hotel Deals

Wyndham Garden Norfolk Downtown
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Jul 7 to Jul 8
CA $137
CA $162 total
Jul 7 - Jul 8
includes taxes & fees
7/10 Good! (1,004 reviews)
"Wonderful, friendly staff"
Reviewed on Jun 21, 2026

Embassy Suites by Hilton Hampton Convention Center
1700 Coliseum Drive Hampton VA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jul 23 to Jul 24
CA $167
CA $195 total
Jul 23 - Jul 24
includes taxes & fees
8.6/10 Excellent! (1,493 reviews)
"Customers should be called or sent a text if room is not an available especially if it will not be available within 30 minutes of checkin (before or after). The refrigerator in my room didn’t work and milk for both an infant and toddler had to be thrown out. Breakfast was good though. The staff was ..."
Reviewed on Jun 22, 2026

Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Fully refundable
The price is CA $160 per night from Jun 30 to Jul 1
CA $160
CA $185 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,015 reviews)
"For the most part the stay was nice, we didn't partake in the breakfast as both mornings it was so crowded, we just went out. The check in and check out was easy and staff was friendly. The room and hotel was very clean and beds comfy. The only complaint we had, was when taking a shower the first ..."
Reviewed on Jun 23, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







