Windsor Holidays from £1,167
Book a Hotel + Flight or Car together to unlock savings
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.
Top Windsor Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Head of Pond House
£1,167
per person
14 Dec - 20 Dec
found 1 day ago
Return flight included
London (LHR) to New Haven (HVN)
10/10 Exceptional! (15 reviews)
The cottage is quaint and old, it is showing its age. The beds were ever comfortable. The entertainment option was not a TV but a projector with a shoddy speaker. The spiral staircase to the upper level was treacherous to come down and several of the vertical supports were look making the decent and ascent scary. The pond side location was very nice and the little patio was special apart from the chainsaws from the unfortunately scheduled tree cutting by neighbors.
Reviewed on 23 Sept 2026
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
HYATT house Hartford North/Windsor
200 Corporate Dr Windsor CT
Fully refundableReserve now, pay when you stay
£117
11 Oct - 12 Oct
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Great, clean quiet place to stay, friendly staff."
Reviewed on 27 Sept 2026
Marriott Hartford/Windsor Airport
28 Day Hill Rd Windsor CT
Fully refundableReserve now, pay when you stay
£147
30 Oct - 31 Oct
includes taxes & fees
8.6/10 Excellent! (1,033 reviews)
"The staff was not so friendly and got woken up by loud noises at 7am"
Reviewed on 27 Sept 2026
Residence Inn by Marriott Hartford/Windsor
100 Dunfey Ln Windsor CT
Fully refundableReserve now, pay when you stay
£107
4 Oct - 5 Oct
includes taxes & fees
8.2/10 Very good! (802 reviews)
"The property has not been maintained. The linens were very worn and uncomfortable. The room appeared clean but then I got some water on the floor in the bathroom and I used a towel to mop it up and the towel turned black with dirt when I wiped up the floor. The person who checked us in Mike I believe ..."
Reviewed on 27 Sept 2026
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.
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.
Northwest Park
7.8/10 (24 reviews)
Explore 473 acres of diverse habitats through 12 miles of scenic trails at this natural retreat. The nature center's educational exhibits and heritage breed farm create an immersive outdoor experience for all ages.
Oliver Ellsworth Homestead
8.2/10 (15 reviews)
Step back in time at Elmwood, home of Oliver Ellsworth who helped draft the US Constitution. Explore period furnishings and family artefacts in this beautifully preserved 18th-century residence.
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.
Windsor Historical Society
8.0/10 (12 reviews)
Step into Connecticut's oldest English settlement at the Windsor Historical Society's museum complex. Explore two historic homes dating to the 1700s and try on colonial costumes in the hands-on learning centre.
Vintage Radio and Communications Museum of Connecticut
7.6/10 (13 reviews)
This time-traveling museum showcases communication technology from the 1800s to modern computers. Tap out Morse code messages and tune vintage radios while knowledgeable volunteers bring history to life.
Windsor Meadows State Park
7.6/10 (10 reviews)
This riverside haven offers peaceful trails winding through floodplain forests with Connecticut River views. Explore the meadows or launch your boat for a day of fishing and serene water adventures.
What to do in Windsor
Connecticut Coloured Regiment Parade Route: An Audio Tour
£7
per adult
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.
