Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $1,599, price is now CA $1,027 per person
CA $1,027
per person
Jan 5 - Jan 7
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,033, price is now CA $1,114 per person
CA $1,114
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 3 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $5,887, price is now CA $3,747 per person
CA $3,747
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $3,821, price is now CA $2,480 per person
CA $2,480
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
9.6/10 Exceptional! (723 reviews)

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

MHO Hotel Bordentown

MHO Hotel Bordentown

2 out of 5
187 US 130 and 206 Bordentown NJ
Fully refundableReserve now, pay when you stay
The price is CA $81 per night from Nov 8 to Nov 9
CA $81
CA $93 total
Nov 8 - Nov 9
includes taxes & fees
MHO Hotel Bordentown
The Heldrich Hotel

The Heldrich Hotel

4 out of 5
10 Livingston Avenue New Brunswick NJ
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Nov 23 to Nov 24
CA $163
CA $193 total
Nov 23 - Nov 24
includes taxes & fees
The Heldrich Hotel
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 $165 per night from Nov 15 to Nov 16
CA $165
CA $189 total
Nov 15 - Nov 16
includes taxes & fees
Hyatt Regency Princeton
See all 395 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,027 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.

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