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.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,842, price is now CA $1,178 per person
CA $1,178
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Hotel was abit dated, however the amount of time you spend in it, it wasn’t a problem, easy access to everywhere. Overall it served its purpose

Reviewed on Jul 1, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,162, price is now CA $2,615 per person
CA $2,615
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Nicely designed hotel with beautiful views. Staff was very nice but service was generally slow.

Reviewed on Jun 28, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,423, price is now CA $1,533 per person
CA $1,533
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,632 reviews)
The hotel is the heart of Times Square. The breakfast was fine. Due to heavy rush during holiday season.

Reviewed on Jun 30, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $3,055, price is now CA $1,935 per person
CA $1,935
per person
Aug 3 - Aug 8
found 7 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
We usually stay at the Ritz but prices were up overall due to the World Cup so we tried this property. It was fantastic and we may have found a new favorite.

Reviewed on Jun 15, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,445, price is now CA $1,549 per person
CA $1,549
per person
Sep 3 - Sep 7
found 6 hours ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,099 reviews)
Excellent service snd breakfast

Reviewed on Jun 30, 2026

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
The price is CA $240 per night from Jul 2 to Jul 3
CA $240
CA $275 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,308 reviews)
"Excellent"

Reviewed on Jul 1, 2026

Hyatt Regency Princeton
Crowne Plaza Princeton-Conference Center by IHG

Crowne Plaza Princeton-Conference Center by IHG

3.5 out of 5
900 Scudders Mill Road Plainsboro NJ
The price is CA $190 per night from Jul 26 to Jul 27
CA $190
CA $218 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (1,014 reviews)
"The property was quiet, clean and isolated while my wife and I prefer especially when it’s our couples trip. The only complaint I have is the refrigerator didn’t cool well and out dated TVs. Over then that my wife and I had great stay we will be back again."

Reviewed on Jun 30, 2026

Crowne Plaza Princeton-Conference Center by IHG
Hilton East Brunswick Hotel & Executive Meeting Center

Hilton East Brunswick Hotel & Executive Meeting Center

3.5 out of 5
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jul 12 to Jul 13
CA $173
CA $199 total
Jul 12 - Jul 13
includes taxes & fees
7.4/10 Good! (1,128 reviews)
"Easy parking and room access."

Reviewed on Jun 30, 2026

Hilton East Brunswick Hotel & Executive Meeting Center
See all 433 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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What to do in Windsor

Audio Tour of Princeton University

Audio Tour of Princeton University

CA $14
per adult
Audio Tour of Princeton University
See all activities in Windsor

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $1,178 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

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