Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in 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 3.320.890 ₫ per night from 1 Sept to 2 Sept
3.320.890 ₫
3.819.023 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Nice"

Reviewed on 7 Aug 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 4.169.139 ₫ per night from 15 Aug to 16 Aug
4.169.139 ₫
4.794.510 ₫ total
15 Aug - 16 Aug
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Lovely stay at the hotel. Restaurant was good and bar had nice selection. Drawback was they said they have room service but wanted to charge me much more to bring the same plastic containers to my room that I walked down to the lobby to get. So I would not call that room service."

Reviewed on 8 Aug 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 3.775.824 ₫ per night from 24 Aug to 25 Aug
3.775.824 ₫
4.342.198 ₫ total
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Beautiful room, very comfortable!"

Reviewed on 11 Aug 2025

HYATT house Hartford North/Windsor
See all 666 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.

Popular places to visit

Northwest Park

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

Frequently asked questions

How much does a Windsor holiday 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 holiday 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 holiday 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 neighbourhoods like Downtown Hartford and North Meadows during your Windsor holiday. Be sure to also add Oliver Ellsworth Homestead and SS&C SummerWind Performing Arts Centre 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 holiday package to Windsor?
Whether you want to check out top sights such as Oliver Ellsworth Homestead and Windsor Meadows State Park on your Windsor holiday, 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 holiday 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 customise 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 travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor getaway by booking a personalised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Windsor?
If you're planning a spur-of-the-moment Windsor holiday, 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 customised Windsor holiday package.