Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 AED 492 per night from Apr 1 to Apr 2
AED 492
AED 566 total
includes taxes & fees
1 Apr - 2 Apr
9/10 Wonderful! (1,011 reviews)
Memorable & Trip of a childs lifetime!!
"This vacation waa a last minute change of plans. 13 year old Daughters birthday. She researched and picked the hotel, and she ended up changing our whole trip, We were supposed to go north, ended up going south. Noone will believe there was a Santa convention that weekend, & she was invited into ..."

Reviewed on 3 March 2025

HYATT house Hartford North/Windsor
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 AED 434 per night from Mar 16 to Mar 17
AED 434
AED 499 total
includes taxes & fees
16 Mar - 17 Mar
8.6/10 Excellent! (1,000 reviews)
Very Solid Stay
"Comfortable bed, spacious room, late checkout (12) was nice. Gym had decent dumbells but they also offer day pass to local gym. Breakfast buffet, although not vast selection, was better quality as we travel often for sports and workers were awesome. Hallway did have a musk, but did not radiate into ..."

Reviewed on 24 February 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 AED 584 per night from Mar 7 to Mar 8
AED 584
AED 672 total
includes taxes & fees
7 Mar - 8 Mar
8.4/10 Very Good! (1,000 reviews)
"Amazing!"

Reviewed on 26 February 2025

Marriott Hartford/Windsor Airport
See all 658 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 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.

Discover the most popular places to visit in Windsor

Northwest Park

4.5/5(4 reviews)

Explore the great outdoors at Northwest Park, a lovely green space in Windsor. Experience the area's great live music or attend a sporting event.

Northwest Park

Oliver Ellsworth Homestead

5/5(4 reviews)

Find out about the history of Windsor with a stop at Oliver Ellsworth Homestead. Experience the area's great live music and acclaimed theater scene.

Oliver Ellsworth Homestead

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