Windsor Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Windsor
Best Western Gateway Grand
4200 NW 97th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
S$121
26 Aug - 27 Aug
includes taxes & fees
Hotel Eleo at the University of Florida
1514 Southwest 14th Street Gainesville FL
Fully refundableReserve now, pay when you stay
S$218
23 Aug - 24 Aug
includes taxes & fees
9.4/10 Exceptional! (1,278 reviews)
"I’m"
Reviewed on 20 Aug, 2026
Drury Inn & Suites Gainesville
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
S$150
25 Aug - 26 Aug
includes taxes & fees
9.6/10 Exceptional! (1,571 reviews)
"It was a clean nice hotel. Our room was facing to the highway, so I could hear the cars all night long. Also, the carpet was WET! I didn't smell anything bad. So, I suppose they just cleaned the carpet. But I couldn't walk around with my bare feet, it was nasty. I mentioned that to the lady at the ..."
Reviewed on 19 Aug, 2026
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 holiday package cost?
We make it easy for everyone to travel, with Windsor holiday packages starting from as low as . You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate escape, why not add a few activities and tours to your itinerary?
How do I get a cheap travel package to Windsor?
Imagine all the thrilling things you could do in Windsor with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into a Windsor holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotels around the globe. Whether you're taking off with the family or surprising your special someone, planning a getaway to Windsor is better with a package.
How far in advance should I book my Windsor holiday?
To score discount prices, book as early as you can. Air carriers typically release tickets, along with some of the lowest fares, up to 12 months ahead of time. Hotels, experiences and car rental should also be booked well in advance so you can have the pick of the bunch. If you were hoping for a last-minute getaway in Windsor, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia Windsor travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your perfect Windsor trip. You can also add on fun things like tours and activities once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll get access to deals you won't find elsewhere.
What should I know before booking a Windsor travel package?
Whether it's relaxation or adventure you're seeking, a Windsor holiday package lets you organise your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Windsor Expedia holiday package?
Most definitely. Expedia has more than 550 airline partners to select from around the globe. With so many choices, finding the right carrier to whisk you away to Windsor will be a snap.
If I'm not able to travel, can I cancel my Windsor holiday package?
If your holiday plans in Windsor have been upended, it's a relief to know that you can amend or cancel your booking. If your booking was made in the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. For more details, check our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
