Windsor Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

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

Top hotels in Windsor

DoubleTree by Hilton Gainesville

DoubleTree by Hilton Gainesville

4 out of 5
3726 Sw 40th Blvd, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is S$126 per night from 21 Aug to 22 Aug
S$126
21 Aug - 22 Aug
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"Close to Shands"

Reviewed on 7 Aug, 2025

DoubleTree by Hilton Gainesville
hom hotel + suites, Trademark Collection by Wyndham

hom hotel + suites, Trademark Collection by Wyndham

2.5 out of 5
3905 Sw 43rd St, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is S$128 per night from 18 Aug to 19 Aug
S$128
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (1,706 reviews)
"Staff were all wonderful. Anything we needed they got on right away."

Reviewed on 2 Aug, 2025

hom hotel + suites, Trademark Collection by Wyndham
Hyatt Place Gainesville Downtown

Hyatt Place Gainesville Downtown

3 out of 5
212 SE 1ST STREET,, Gainesville, FL
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 24 Aug to 25 Aug
S$165
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,036 reviews)
"This hotel is awesome. From the moment you step in the hotel to when you exit. Everyone is courteous , all the hotel is super clean and the vibe is above extraordinary. The breakfast is abundant and delicious. I highly recommend it. It won’t disappoint you."

Reviewed on 5 Aug, 2025

Hyatt Place Gainesville Downtown
See all 781 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.

Popular places to visit

Shands at the University of Florida

If Shands at the University of Florida is what brings you to town, hopefully you'll have a chance to explore more of Gainesville.

Shands at the University of Florida

Sante Fe College

Explore the campus of Sante Fe College during your trip to Gainesville. You can attend a sporting event while in the area.

Sante Fe College

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.