Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NT$5,067 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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    Plan, book, and manage your trip all in one place

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport
3 out of 5
555 Corporate Dr, Windsor, CT
The price is NT$4,197 per night from Jul 20 to Jul 21
NT$4,197
NT$4,826 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"The view was stunning and the hotel was very clean. Would definitely stay again"

Reviewed on 2025/6/18

Hilton Garden Inn Hartford North/Bradley Int'l Airport
Marriott Hartford/Windsor Airport
Marriott Hartford/Windsor Airport
3.5 out of 5
28 Day Hill Rd, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NT$4,938 per night from Aug 8 to Aug 9
NT$4,938
NT$5,678 total
Aug 8 - Aug 9
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Staff friendly, hotel was clean, spacious room. Breakfast not included."

Reviewed on 2025/6/22

Marriott Hartford/Windsor Airport
Residence Inn by Marriott Hartford/Windsor
Residence Inn by Marriott Hartford/Windsor
3 out of 5
100 Dunfey Ln, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is NT$4,412 per night from Jul 27 to Jul 28
NT$4,412
NT$5,073 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (614 reviews)
"Very good"

Reviewed on 2025/7/8

Residence Inn by Marriott Hartford/Windsor
See all 677 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.

Discover the most popular places to visit in Windsor

Windsor Historical Society

5/5(4 reviews)

You can spend an afternoon browsing the exhibits at Windsor Historical Society during your trip to Windsor. Experience the great live music or attend a sporting event in this family-friendly area.

Windsor Historical Society

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices on Expedia for your Windsor break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
You can typically find lower rates and greater availability in December, January and February. Explore our cheap Windsor vacation packages and you could score some great off-season discounts.
How many days is enough for Windsor?
With about 2 days, you'll have enough time to visit popular neighborhoods like Downtown Hartford and North Meadows during your Windsor vacation. Be sure to also add Oliver Ellsworth Homestead and SS&C SummerWind Performing Arts Center to your list of must-sees. In the mood for more adventures? Consider exploring outside of Windsor on tours and day trips.
Is it worth booking a vacation package to Windsor?
Whether you want to check out top sights such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor vacation, or coming for its great history, festivals and culture, there's something for everyone here. With so many things to see and do, you'll quickly learn why so many visitors think Windsor is a good vacation destination.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Pick your travel dates: What you want to do in Windsor and your preferred season will help you decide when to go.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Windsor.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.