Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 ¥18,609 per night from Aug 3 to Aug 4
¥18,609
¥21,959 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,024 reviews)
"The place was clean and staff was very friendly."

Reviewed on Jul 26, 2025

Holiday Inn Binghamton Downtown by IHG
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
569 Harry L Dr, Johnson City, NY
Fully refundableReserve now, pay when you stay
The price is ¥13,683 per night from Aug 24 to Aug 25
¥13,683
¥15,461 total
Aug 24 - Aug 25
includes taxes & fees
7.2/10 Good! (425 reviews)
Clean and comfortable stay
"Comfortable stay and clean hotel. The check in and checkout was quick. The front desk was very helpful. The breakfast was good, had hot sausages and scrambled eggs apart from other regular items. The AC could have been better but it was not bad. The hotel was quiet and worth what we paid for. Definitely ..."

Reviewed on Jul 23, 2025

Comfort Inn & Suites
DoubleTree by Hilton Hotel Binghamton

DoubleTree by Hilton Hotel Binghamton

4 out of 5
225 Water St, Binghamton, NY
Fully refundableReserve now, pay when you stay
The price is ¥19,960 per night from Aug 3 to Aug 4
¥19,960
¥23,553 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"B+"

Reviewed on Jul 21, 2025

DoubleTree by Hilton Hotel Binghamton
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.

Frequently asked questions

How much does a Windsor vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Windsor costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Windsor?
Plan your getaway for the off-season and you're likely to find cheap Windsor vacation packages. Keep in mind that public holidays and major events and festivals can impact prices, so do some research before you go.
How many days is enough for Windsor?
Typically, a handful of days is enough to see the top attractions during your Windsor vacation. But if you'd like to have time to relax or take day trips, consider extending your itinerary.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windsor package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor escape underway.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Windsor?
If you've got your Windsor vacation dates finalized, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Windsor?

  1. Choose your travel dates: What you'd like to do in Windsor and your favorite season will help you decide when to go.
  2. Set a budget: Factor in expenses such as flights, transportation and food when working out how much to save for your trip to Windsor. Then, select a hotel that works with your budget, whether that's an affordable option or a more upscale retreat.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Windsor. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the right Windsor vacation package for you.

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