Windsor Vacation Packages

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

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Your Windsor Vacation

Our Windsor vacation packages provide endless opportunities to discover new sights, sounds and sensations. And with all the travel planning taken care of, you'll be free to enjoy your city adventure without a worry in the world. Fill your trip to Windsor with visits to its big-hitting attractions. Where to first? Make a move for Animal Adventure Park. Don't delay visiting this city any longer. Your perfect Windsor vacation is a couple of clicks away with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Sayre by IHG

Candlewood Suites Sayre by IHG

2.5 out of 5
Price was CA $586, price is now CA $570 per person
CA $570
per person
Dec 18 - Dec 20
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Binghamton (BGM)
8.8/10 Excellent! (789 reviews)
The room was clean ,well appointed bed and pillows were very comfortable. Best hotel of our entire trip . Full size refrigerator was a surprise. Wish all our accommodations were this nice during our trip. Price was very reasonable also. Next trip we will seek out the IHG hotels.

Reviewed on Nov 1, 2026

Crystal Springs Inn and Suites

Crystal Springs Inn and Suites

2 out of 5
Price was CA $678, price is now CA $667 per person
CA $667
per person
Dec 18 - Dec 20
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Binghamton (BGM)
9.2/10 Wonderful! (271 reviews)

Holiday Inn Binghamton Downtown by IHG

Holiday Inn Binghamton Downtown by IHG

3 out of 5
Price was CA $1,976, price is now CA $1,956 per person
CA $1,956
per person
Dec 19 - Dec 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Binghamton (BGM)
8.4/10 Very good! (1,005 reviews)

Comfort Inn Apalachin / Binghamton W Route 17

Comfort Inn Apalachin / Binghamton W Route 17

2.5 out of 5
Price was CA $577, price is now CA $573 per person
CA $573
per person
Dec 18 - Dec 20
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Binghamton (BGM)
7.8/10 Good! (1,005 reviews)

Comfort Inn & Suites Sayre

Comfort Inn & Suites Sayre

3 out of 5
Price was CA $638, price is now CA $637 per person
CA $637
per person
Dec 18 - Dec 20
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Binghamton (BGM)
8.8/10 Excellent! (1,002 reviews)

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Waterfront Properties vacation rental

Waterfront Properties vacation rental

Windsor NY
The price is CA $203 per night from Nov 4 to Nov 5
CA $203
CA $497 total
Nov 4 - Nov 5
includes taxes & fees
Waterfront Properties vacation rental
Microtel Inn & Suites By Wyndham Binghamton

Microtel Inn & Suites By Wyndham Binghamton

2.5 out of 5
400 Prospect Street Binghamton NY
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Nov 9 to Nov 10
CA $124
CA $143 total
Nov 9 - Nov 10
includes taxes & fees
Microtel Inn & Suites By Wyndham Binghamton
Holiday Inn Binghamton Downtown by IHG

Holiday Inn Binghamton Downtown by IHG

3 out of 5
2-8 Hawley Street Binghamton NY
Fully refundable
The price is CA $165 per night from Nov 23 to Nov 24
CA $165
CA $195 total
Nov 23 - Nov 24
includes taxes & fees
Holiday Inn Binghamton Downtown by IHG
See all 417 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

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this destination from CA $570 on Expedia. However, how much your vacation to Windsor costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Windsor?
To score cheap Windsor vacation packages, plan your getaway outside of peak times like public holidays and major festivals. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Windsor?
With a well-organized schedule, you can easily visit the main Windsor sights in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Finding a cheap Windsor package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Windsor package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can customize your Windsor trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor vacation dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Windsor?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Windsor.
  2. Figure out your budget: Make sure you have enough money to cover everything from dining out and transportation to activities and flights. Your hotel will likely be the biggest expense during your trip to Windsor.
  3. Decide how long to go away for: Now that you're more familiar with Windsor, you can work out the perfect length of your break. Put together a draft plan and give yourself enough time to cover everything you want to see.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose 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.