Windsor Vacation Packages
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Your Windsor Vacation
When you book a vacation package to Windsor, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Discover the many delights of this vibrant city from your base in a neighborhood like Princeton Meadows, which is great for golfing. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to begin exploring is Working Dog Winery. Whoever you're escaping with and whatever you plan to spend, your dream Windsor vacation is just a few clicks away with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane
CA $1,535
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
Cozy Home near City Center with Hot tub
South Philadelphia
CA $4,138
per person
Oct 2 - Oct 5
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Philadelphia (PHL)
10/10 Exceptional! (3 reviews)
This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available. Thank you!
Reviewed on Mar 2, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
CA $162
CA $186 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (1,404 reviews)
"The hotel was okay. For the money spent, I think it could have included breakfast. The pull out bed’s mattress was flat and looked like it didn’t fit the bed. We had to ask for more linen and towels even though I had already mentioned how many guests would be in the room. The toilet flushed really ..."
Reviewed on Aug 24, 2026
Hilton East Brunswick Hotel & Executive Meeting Center
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
CA $151
CA $173 total
Sep 10 - Sep 11
includes taxes & fees
7.4/10 Good! (1,255 reviews)
"Wonderful stay"
Reviewed on Aug 24, 2026
Holiday Inn East Windsor - Cranbury Area by IHG
399 Monmouth St Hightstown NJ
Fully refundable
CA $128
CA $147 total
Sep 6 - Sep 7
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
"Room was freezing and unenjoyable. Both my kids got sick from the air conditioning. We called up the maintenance staff twice to help us out but couldn't over come the cold air"
Reviewed on Aug 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.
What to do in Windsor
Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals from CA $1,496 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
January, February and March are great times to look for cheap Windsor vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and accommodations.
How many days is enough for Windsor?
With a well-organized travel plan, you can easily tick off the top Windsor sights in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Windsor package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor adventure underway.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Windsor trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor travel dates finalized, book as early as you can to grab some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Windsor?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Windsor.
- Budget wisely: Besides the price of your accommodations, you should factor in other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could arise during your trip to Windsor.
- Decide how long to go for: Now that you know more about Windsor, you can work out the right length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to do.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left 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.
