Windsor Holidays from AU$4,162

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.

The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was AU$5,414, price is now AU$4,162 per person
AU$4,162
per person
20 Oct - 27 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to New Haven (HVN)
No reviews

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$246 per night from 28 Aug to 29 Aug
AU$246
28 Aug - 29 Aug
includes taxes & fees
8.4/10 Very good! (1,014 reviews)
"I loved how easy check in and out was. The room was very clean. And we had amazing breakfast. With the nicest woman whom waited on us"

Reviewed on 28 July 2026

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$262 per night from 15 Aug to 16 Aug
AU$262
15 Aug - 16 Aug
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Fantastic experience. The breakfast was great! highly Recommended."

Reviewed on 30 July 2026

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 AU$202 per night from 7 Aug to 8 Aug
AU$202
7 Aug - 8 Aug
includes taxes & fees
Hilton Garden Inn Hartford North/Bradley Int'l Airport
See all 751 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

Windsor Arts Center

7.6/10 (18 reviews)
This historic freight house turned art centre showcases contemporary New England art in a charming railway setting. Enjoy rotating exhibitions while soaking in the creative atmosphere of Windsor's cultural hub.
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 from AU$4,162 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.