Windsor Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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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
Fully refundableReserve now, pay when you stay
The price is ₩175,507 per night from Sep 1 to Sep 2
₩175,507
₩201,833 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"NICE STAFF, GREEN HOTEL, GREAT BAR AND RESTAURANT."

Reviewed on Aug 1, 2025

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 ₩220,336 per night from Aug 15 to Aug 16
₩220,336
₩253,386 total
Aug 15 - Aug 16
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Nice and clean"

Reviewed on Aug 3, 2025

Marriott Hartford/Windsor Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is ₩199,549 per night from Aug 17 to Aug 18
₩199,549
₩229,481 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Spacious and clean. Staff was kind."

Reviewed on Aug 3, 2025

HYATT house Hartford North/Windsor
See all 667 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.

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.