Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Your Windsor Holiday

Well known for its cosmopolitan vibe and rich history, Windsor is a fabulous getaway destination. Book one of our Windsor holiday packages and enjoy all that this fascinating city has to offer. If your trip to Windsor includes a little sightseeing, don't miss renowned attractions like XL Centre, Xfinity Theatre and University of Hartford. Whoever you're escaping with and whatever you want to spend, your dream Windsor holiday is just clicks away with Expedia.

Windsor Holiday

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
28,800
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Xfinity Theatre, Connecticut Science Centre and Nomads Adventure Quest

Our pick of the best Windsor Hotel Deals

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 AU$259 per night from 20 Nov to 21 Nov
AU$259
20 Nov - 21 Nov
includes taxes & fees
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 AU$244 per night from 24 Nov to 25 Nov
AU$244
24 Nov - 25 Nov
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The shampoo, conditioner and body wash in the shower was very unappealing. The hotel room was so nice except for the shower area. The food at the bar was also not great. The room itself was such a nice setup and comfortable and clean. Service was very good and nice people."

Reviewed on 29 Oct 2026

HYATT house Hartford North/Windsor
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
The price is AU$229 per night from 1 Nov to 2 Nov
AU$229
1 Nov - 2 Nov
includes taxes & fees
Courtyard By Marriott Hartford/Windsor Airport
See all 807 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Windsor attractions

Loomis Chaffee School

This prestigious New England boarding school blends historic architecture with state-of-the-art facilities. Schedule a guided campus tour to experience Loomis Chaffee's innovative learning spaces and picturesque grounds.
See properties

What to do in Windsor

Connecticut Coloured Regiment Parade Route: An Audio Tour

Connecticut Coloured Regiment Parade Route: An Audio Tour

AU$14
per adult
Connecticut Coloured Regiment Parade Route: An Audio Tour
See all activities in Windsor

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.

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