Windsor Vacations from $267
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
$1,138
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
We stayed in one of the cottages and it was just perfect. The fully equipped kitchen downstairs with a master suite was perfect for my parents. I appreciated having the laundry upstairs with the other bedrooms.
The staff at the main building were so helpful with our packages and printing documents for us.
Unfortunately we had a very busy week and could not enjoy the wonderful amenities of the resort.
Overall, a great selection and would start again!
Reviewed on Sep 25, 2026
What to do in Windsor
Interlachen: Rodman Reservoir Trophy Bass Fishing Trip
$435
per adult
Windsor Hotel Deals
Drury Inn & Suites Gainesville
4000 Southwest 40th Blvd Gainesville FL
Fully refundableReserve now, pay when you stay
$105 nightly
$118 total
Oct 7 - Oct 8
Total with taxes and fees
9.6/10 Exceptional! (1,630 reviews)
"Surprisingly good price, cozy quiet and clean. Will recommend for the traveler. Courteous check in without any hiccups."
Reviewed on Oct 1, 2026
Sleep Inn & Suites University/Shands
4110 SW 40th Boulevard Gainesville FL
Fully refundable
$81 nightly
$91 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,304 reviews)
"It was amazing"
Reviewed on Sep 30, 2026
Country Inn & Suites by Radisson, Gainesville, FL
4015 Sw 43rd St Gainesville FL
Fully refundable
$88 nightly
$99 total
Oct 12 - Oct 13
Total with taxes and fees
9.2/10 Wonderful! (2,017 reviews)
"Room was dirty. Yellow linens in areas, blood stains on pillow case. The furniture was worn. Looked like it was from a garage sale."
Reviewed on Oct 1, 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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Gainesville Regional Airport (GNV) |
Top Sights | Florida Museum of Natural History, University of Florida Bat Houses and Hippodrome State Theatre |
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Frequently asked questions
How much does a Windsor vacation package cost?
You can grab a vacation package to this destination from $267 on Expedia. But how much your vacation to Windsor costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
September, October and December are the best times to look for cheap Windsor vacation packages. Choosing to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Windsor?
The ideal duration of your Windsor vacation depends on what you'd like to see. Generally, a few days to a week will give you time to visit all the top attractions and explore some hidden spots along the way.
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 apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Windsor package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Windsor?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Windsor getaway.
How to plan a trip to Windsor?
- Choose your dates: The things you want to do in Windsor and your favorite season will help you decide when to travel.
- Set your budget: Factor in expenses such as flights, transportation and food when working out how much to set aside for your trip to Windsor. Then, choose a hotel that works with your budget, whether that's an economical option or a more luxurious getaway.
- Explore Windsor with our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Windsor. You can also save your must-visit places, collaborate with family and friends and arrange all your plans in one place.
- Work out your trip length: Consider how much time you want to spend discovering Windsor. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Windsor vacation package.
- Book experiences or activities in advance: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on the best Windsor has to offer. Find all the fun things to do in Windsor with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the 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 cheap 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.