Windsor Vacations from $363

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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.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $780, price is now $363 per person
$363
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Ran out of hot water a few times it was immediately addressed. Other than that nice place will stay again.

Reviewed on Apr 12, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $1,131, price is now $419 per person
$419
per person
Jun 13 - Jun 19
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (6,071 reviews)
Clean room, staff was nice and helpful when needed.

Reviewed on Apr 12, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,446, price is now $608 per person
$608
per person
Jun 13 - Jun 19
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,233 reviews)
I enjoyed how comfortable my room was. Spacious and modern and clean. Thank you

Reviewed on Apr 10, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $852, price is now $392 per person
$392
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,554 reviews)
$25 dollars for person to enter the water park. That’s insane.

Reviewed on Apr 12, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $797, price is now $370 per person
$370
per person
May 23 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,836 reviews)
I had to wait three hours for check-in didn’t get checked in till 6 o’clock that afternoon . They are over booking and under staff.

Reviewed on Apr 12, 2026

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Discover the most popular places to visit in Windsor

A distant view of The University of Florida in the morning

University of Florida

4.5/5(845 reviews)

Take a campus tour or just explore the area around University of Florida, a top college in Gainesville. Stroll along the lakeside or attend a sporting event in the area.

University of Florida
Ben Hill Griffin Stadium

Ben Hill Griffin Stadium

4.5/5(274 reviews)

Catch an event at Ben Hill Griffin Stadium during your trip to Gainesville. Stroll along the lakeside or attend a sporting event in the area.

Ben Hill Griffin Stadium
Peleides blue morpho butterfly

Florida Museum of Natural History

4.5/5(174 reviews)

You can spend an afternoon exploring the galleries in Florida Museum of Natural History during your trip to Gainesville. You can attend a sporting event while in the area.

Florida Museum of Natural History

Windsor Hotel Deals

HOM Hotel Gainesville, SureStay Collection by Best Western

HOM Hotel Gainesville, SureStay Collection by Best Western

2.5 out of 5
3905 Sw 43Rd St Gainesville FL
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $87 total per night from Apr 19 to Apr 20
$87 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,878 reviews)
Clean room but very basic. Good for the money. Need some updates on window coverings. New shower tiles I think but no shelf to put shampoo on. Beds were fine. Breakfast was normal hotel free breakfast.

Reviewed on Apr 12, 2026

HOM Hotel Gainesville, SureStay Collection by Best Western
Country Inn & Suites by Radisson, Gainesville, FL

Country Inn & Suites by Radisson, Gainesville, FL

3 out of 5
4015 Sw 43rd St Gainesville FL
Fully refundable
$88 nightly
The price is $99 total per night from Apr 19 to Apr 20
$99 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,759 reviews)
The staff was very nice but the room was outdated.

Reviewed on Apr 12, 2026

Country Inn & Suites by Radisson, Gainesville, FL
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
$97 nightly
The price is $109 total per night from Apr 26 to Apr 27
$109 total
Apr 26 - Apr 27
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
Clean rooms and facilities. Great staff

Reviewed on Apr 8, 2026

DoubleTree by Hilton Gainesville
See all 888 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.

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 $363 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?

  1. Choose your dates: The things you want to do in Windsor and your favorite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.