Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Windsor Vacation
Take the stress out of organizing your next exciting adventure with a Windsor vacation package. Whether you're lured here by its history, food or other highlights, this city offers endless possibilities for fun. Every trip to Windsor should include a little sightseeing. Kates Fish Camp is an excellent place to start. No matter your travel plans or budget, organizing a tailored Windsor vacation is a cinch with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Drury Inn & Suites Gainesville
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
CA $147
CA $165 total
Nov 26 - Nov 27
includes taxes & fees
Country Inn & Suites by Radisson, Gainesville, FL
4015 Sw 43rd St Gainesville FL
Fully refundable
CA $124
CA $139 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (2,036 reviews)
"Clean room"
Reviewed on Oct 25, 2026
Sleep Inn & Suites University/Shands
4110 SW 40th Boulevard Gainesville FL
Fully refundable
CA $112
CA $134 total
Nov 15 - Nov 16
includes taxes & fees
8.8/10 Excellent! (1,323 reviews)
"Average hot breakfast. Free coffee and popcorn in the lobby.. The only thing is the property is somewhat old and needs new update- carpets, wall paper and decor are old style. Close to UF., behind Drury Inn and Suites."
Reviewed on Oct 25, 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.
What to do in Windsor
Interlachen: Rodman Reservoir Trophy Bass Fishing Trip
CA $615
per adult
Frequently asked questions
How much does a Windsor vacation package cost?
We make it easy for everyone to travel, with Windsor vacation packages starting from as low as CA $788. You'll have the flexibility to combine your favorite 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 vacation 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 vacation?
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 vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Windsor Expedia vacation 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 vacation package?
If your vacation 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.
