Windsor Vacations from $283

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Kiteville Owego

Kiteville Owego

2 out of 5
Price was $322, price is now $283 per person
$283
per person
Nov 7 - Nov 10
found 3 hours ago
Roundtrip flight included
New York (JFK) to Binghamton (BGM)
8.2/10 Very Good! (377 reviews)
Parking lot is lit up at night so you feel safe. The other patrons are friendly and respectful. Aldis is right across the parkong lot for easy food shopping and everyrhing you need is walkable

Reviewed on Sep 26, 2025

Hampton Inn Owego

Hampton Inn Owego

2.5 out of 5
Price was $385, price is now $341 per person
$341
per person
Nov 7 - Nov 10
found 3 hours ago
Roundtrip flight included
New York (JFK) to Binghamton (BGM)
9/10 Wonderful! (575 reviews)
I really enjoyed my stay at this hotel. The place is very clean, beautifully kept, and the staff is extremely friendly and helpful. The rooms are lovely and comfortable, and overall the atmosphere is very pleasant. I didn’t give five stars because, although I called ahead to confirm the pool was open, I wasn’t informed that the heating system wasn’t working. It made the water quite cold, and I got the impression that perhaps the heating is turned off when there aren’t many guests. Either way, it was disappointing since the pool was one of the reasons I chose this hotel. Another small detail is the bathroom towels—they’re very small (around 20 inches). I would recommend bringing your own towels or asking for the larger ones available by the pool. That being said, it’s a beautiful hotel with excellent service, and I would definitely recommend it to others.

Reviewed on Sep 19, 2025

Microtel Inn And Suites Sayre PA

Microtel Inn And Suites Sayre PA

2 out of 5
Price was $367, price is now $338 per person
$338
per person
Nov 7 - Nov 10
found 3 hours ago
Roundtrip flight included
New York (JFK) to Binghamton (BGM)
8/10 Very Good! (956 reviews)
Business-friendly | Shops nearby | Parking | Breakfast

Reviewed on Sep 12, 2025

Best Western Owego Inn

Best Western Owego Inn

2.5 out of 5
Price was $379, price is now $360 per person
$360
per person
Nov 7 - Nov 10
found 3 hours ago
Roundtrip flight included
New York (JFK) to Binghamton (BGM)
8.4/10 Very Good! (967 reviews)
Room 237 bathroom sink drain stuck

Reviewed on Sep 27, 2025

Comfort Inn Apalachin / Binghamton W Route 17

Comfort Inn Apalachin / Binghamton W Route 17

2.5 out of 5
Price was $358, price is now $342 per person
$342
per person
Nov 7 - Nov 10
found 3 hours ago
Roundtrip flight included
New York (JFK) to Binghamton (BGM)
8/10 Very Good! (977 reviews)
The guy at the front desk was very friendly ! Easy check in. Nice comfortable room. Would stay again!

Reviewed on Sep 18, 2025

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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
$109 nightly
The price is $129 total per night from Oct 30 to Oct 31
$129 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,019 reviews)
"Location Location Location"

Reviewed on Sep 22, 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
$84 nightly
The price is $95 total per night from Oct 5 to Oct 6
$95 total
Oct 5 - Oct 6
Total with taxes and fees
7.4/10 Good! (512 reviews)
"safe place to stay"

Reviewed on Sep 23, 2025

Comfort Inn & Suites
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
$108 nightly
The price is $122 total per night from Oct 1 to Oct 2
$122 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (1,103 reviews)
"Finding the driveway is a bit tricky but the Microtel Binghamton, where I have now stayed twice, is one of best run hotels I have ever visited."

Reviewed on Sep 24, 2025

Microtel Inn & Suites By Wyndham Binghamton
See all 346 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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Frequently asked questions

How much does a Windsor vacation package cost?
Offering excellent value package deals from $283 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?
If you're hoping to snag a cheap Windsor vacation package, consider visiting in January, September and December. You're likely to find lower prices on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Windsor?
Typically, a handful of days is enough to visit the major attractions during your Windsor vacation. But if you prefer to have more time to unwind or go on day tours, think about extending your trip.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Windsor trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.