Windsor Holidays

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Your Windsor Holiday

The cosmopolitan vibe and rich history are just the beginning of the things Windsor has going for it. Enjoy the best parts of this fascinating city your way with a personalised Windsor holiday package. A trip to Windsor is an ideal opportunity to see the sights. Be sure to stop by big-name attractions such as XL Centre, Xfinity Theatre and University of Hartford. Whatever your travel plans or budget, putting together the ultimate tailored Windsor holiday is simple with Expedia.

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

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 £122 per night from 20 Jul to 21 Jul
£122
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"The view was stunning and the hotel was very clean. Would definitely stay again"

Reviewed on 18 Jun 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 £144 per night from 8 Aug to 9 Aug
£144
8 Aug - 9 Aug
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Staff friendly, hotel was clean, spacious room. Breakfast not included."

Reviewed on 22 Jun 2025

Marriott Hartford/Windsor Airport
Residence Inn by Marriott Hartford/Windsor
Residence Inn by Marriott Hartford/Windsor
3 out of 5
100 Dunfey Ln, Windsor, CT
Fully refundableReserve now, pay when you stay
The price is £129 per night from 27 Jul to 28 Jul
£129
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very Good! (614 reviews)
"Very good"

Reviewed on 8 Jul 2025

Residence Inn by Marriott Hartford/Windsor
See all 674 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Windsor holiday with Expedia?
With excellent-value flights, hotel and car hire options all in one place, Expedia makes planning your Windsor getaway hassle-free. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Select from fabulous retreats, add your flights and/or a car hire (and maybe even some exciting tours and activities!) and land incredible prices. Need to change plans? Expedia has a flexible cancellation policy for many bookings. To discover more, make your way to our Customer Service Portal link.
When is the best time of year to holiday in Windsor?
If you want to experience the buzz of Windsor during peak season, book your getaway for March, May and August. December, January and February are usually the quietest months of the year. To give you an idea of what type of weather you can experience, the daytime average temperature in January, the coolest time of year in Windsor, is -2ºC. The warmest period here is July, when temperatures are around 23ºC.
What is the top hotel for my holiday in Windsor?
Offering many of the creature comforts of home, The Inn at Mystic will make the perfect base for your Windsor getaway.
How do I get a cheap holiday to Windsor?
One of the easiest ways to save pounds (and time) is to bundle your bookings with Expedia. Hotels, hire cars, flights and activities --- we've got them all covered. Choose the combination that suits your style and watch your savings stack up. Of course, holidays are never a one-size-fits-all. That's why Expedia offers over 400 partner airlines and 321,000 hotels throughout the world, so you can customise your Windsor holiday your way. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Windsor holiday?
There's an almost endless list of things to see and do while enjoying a holiday in Windsor. Trinity College, Mark Twain House & Museum, Bushnell Park and University of Connecticut-Hartford are a few of this city's best attractions.
What is the best area to stay in when on holiday in Windsor?
There's so much to do in Windsor, so stay near its top attractions and spend more time sightseeing. Northwest Park is one place to add to your to-do list.
Do I need a visa for my Windsor holiday?
Research the latest rules on official government websites. Your nationality and whether you're travelling for study, leisure or business will determine if you need a visa for Windsor. Get familiar with the application process, including any required documentation, turnaround times and fees. Start your application well in advance to allow enough time for processing. Some visas may take weeks or even months to go through, depending on the country and time of year.
What should I wear on my Windsor holiday?
Do a little research into the types of things people in Windsor wear, and consider browsing style blogs for some fashion inspiration. Try to create a versatile wardrobe filled with pieces that suit your destination and show off your unique sense of style. Daytime temperatures during January, Windsor's coolest month, are around -2ºC. July marks this destination's warmest month when the average daily temperature reaches 23ºC. Our advice? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Windsor holiday include?
Flights, hotels and a cool car for all your road trip adventures. Simply select your favourite bundle and get access to incredible deals. Once you've made your booking, add on a few tours and activities and watch your savings grow. When it comes to planning your Windsor break, the choice is all yours! Explore a large selection of property types and choose one that matches your group size. The most popular rentals here are private holiday homes and hotels. With Expedia, it's easy to customise your Windsor escape however you like.
Does Expedia offer Book Now, Pay Later Windsor holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in instalments. Simply select the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers the ability to pay in multiple instalments that fit all budgets, so you can have that well-deserved holiday sooner.
  • No-deposit holidays: When you stumble on an amazing deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your escape.

Can I choose my airline with a Windsor Expedia holiday?
Yes --- and it's easy too. Expedia has access to more than 400 partner airlines around the world. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.