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*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $1,745, price is now CA $995 per person
CA $995
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,820 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $3,494, price is now CA $2,032 per person
CA $2,032
per person
Sep 15 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,226 reviews)

5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was CA $5,636, price is now CA $3,380 per person
CA $3,380
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (5 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,637, price is now CA $1,586 per person
CA $1,586
per person
Oct 12 - Oct 16
found 16 hours ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
The Wi- Fi posed some difficulties but other than that everything else was fine

Reviewed on Jul 27, 2026

The High Line Hotel

The High Line Hotel

4 out of 5
Manhattan
Price was CA $2,327, price is now CA $1,465 per person
CA $1,465
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,014 reviews)
Beautiful building, wonderful location, but most rooms do not have air-conditioning. I was lucky enough to get a lovely corner room with an air conditioner, but the lobby and patio were filled with people complaining the hotel did not have air-conditioning and the and the majority of the rooms do not have a built-in unit, as I did. The staff could not have been nicer, when there was a problem with my hot water they sent somebody right up. I would stay here again in a heartbeat, but I would insist on a room with air-conditioning.

Reviewed on Jul 26, 2026

Ready to book your vacation to Windsor?

 

Choose your dates

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 $227 per night from Aug 10 to Aug 11
CA $227
CA $260 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,347 reviews)
"Great place to stay!"

Reviewed on Jul 26, 2026

Hyatt Regency Princeton
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 $172 per night from Aug 10 to Aug 11
CA $172
CA $197 total
Aug 10 - Aug 11
includes taxes & fees
7.4/10 Good! (1,194 reviews)
"The hotel needs updating!"

Reviewed on Jul 27, 2026

Hilton East Brunswick Hotel & Executive Meeting Center
Radisson Hotel Freehold

Radisson Hotel Freehold

3.5 out of 5
50 Gibson Pl Freehold NJ
Fully refundable
The price is CA $210 per night from Aug 19 to Aug 20
CA $210
CA $241 total
Aug 19 - Aug 20
includes taxes & fees
Radisson Hotel Freehold
See all 410 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 $995 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.