Windsor Vacation Packages
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Your Windsor Vacation
With a vacation package to Windsor, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time discovering this awesome city. During your trip to Windsor, set aside some time for sightseeing. One of the best places to start exploring is Historic Hope Plantation. Check out Expedia's extensive range of travel options and start planning your dream vacation to Windsor today.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Williamston Inn NC Near Greenville US 64
Price was CA $1,071, price is now CA $1,017 per person
CA $1,017
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greenville (PGV)
8/10 Very Good! (24 reviews)
The room and bathroom were clean. The room was spacious. Water pressure and temperature was great. Mattress was comfortable but the bed platform made a loud metal rumbling noise every time we got out of bed, not great for light sleepers. Check in took a long time because they had a new system that the night clerk hadn’t been trained on very well. She was very nice and apologetic about the wait, but also made a slightly snarky comment about our diesel truck running outside. The bathroom had very little vanity space to sit a makeup bag and no electrical outlets. I wound up getting ready in the bedroom area at a small table where there was another mirror and I could sit my bag. Overall a good stay for a night or two.
Reviewed on Apr 26, 2026
Red Roof Inn Greenville, NC
Price was CA $1,046, price is now CA $1,019 per person
CA $1,019
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greenville (PGV)
4.8/10 (271 reviews)
Upon arrival the gentleman at the front was very kind and accommodating. It was a nice room very clean
My only complaint is the night desk lady who gave my boyfriend her phone number to hang out together. Kinda disrespectful but other then that very comfy!! Thank you
Reviewed on Feb 23, 2026
Windsor Hotel Deals
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn
Merry Hill NC
The price is CA $566 per night from Jun 7 to Jun 8
CA $566
CA $852 total
Jun 7 - Jun 8
includes taxes & fees
6/10 (1 review)
Washing machine brokenMinimal kitchen untensils (no restaurants close )Was unaware the rooms are adjacent to the office area. Employees are able to walk around the living space. Each room has an individual key. This information should be shared with renters.
Reviewed on Mar 7, 2026
"Country Farm House"
Windsor NC
10/10 Exceptional! (27 reviews)
Very clean house. Host was awesome. Enjoyed our fishing trip.
Reviewed on Apr 19, 2026
Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122
Windsor NC
The price is CA $430 per night from May 12 to May 13
CA $430
CA $684 total
May 12 - May 13
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.
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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.
