Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to £335 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Packages with flights are ATOL protected

Your Windsor Holiday

Food, history, entertainment and more … There's so much to experience with a Windsor holiday package. And with the ability to customise your city break, you know it'll be one that's hard to forget. If sightseeing is on the agenda during your trip to Windsor, stop by leading attractions like Mount Ascutney, Blow-Me-Down Bridge and Mt Ascutney State Park. Whoever you're escaping with and whether your budget is big or small, your ultimate Windsor holiday is only clicks away with Expedia.

Windsor Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
2,100
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Mt Ascutney State Park, Harpoon Brewery and Quechee State Park

Top hotels in Windsor

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is £97 per night from 7 Sept to 8 Sept
£97
7 Sept - 8 Sept
includes taxes & fees
7/10 Good! (1,002 reviews)
"The staff was the best part of this stay. They were friendly and welcoming. The room was very spacious and comfortable for the price."

Reviewed on 13 Aug 2025

White River Inn and Suites
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road, West Lebanon, NH
Fully refundableReserve now, pay when you stay
The price is £124 per night from 24 Aug to 25 Aug
£124
24 Aug - 25 Aug
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"The pool looks great. Kids were having fun."

Reviewed on 16 Aug 2025

Fireside Inn & Suites West Lebanon
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is £364 per night from 1 Sept to 2 Sept
£364
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul 2025

Woodstock Inn & Resort
See all 2,574 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

How much does a Windsor travel package cost?
Discover the best of Windsor from as low as . Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can score even more discounts when you add a few sightseeing activities to your package.
If I'm not able to travel, can I cancel my Windsor travel package?
It's difficult to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Windsor?
Combine your hotels and flights, add extras such as a rental car or activities, and save with a Windsor travel package. You won't just pick up superb discounts on your trip — you'll have plenty of choice within your reach too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 properties around the world. Your next affordable adventure starts right here, right now!
Does Expedia offer Book Now, Pay Later Windsor holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Don't forget to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all types of budgets, so you can have that well-earned holiday now.
  • Pay in instalments holidays: If you'd prefer to pay for your escape across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is much easier with this payment option. Just put down a small deposit on your escape and then start working on your travel plans.

Where should I stay in Windsor?
With lots to discover in Windsor, it'd be convenient for you to stay near its attractions. Harpoon Brewery, American Precision Museum and South Congregational Church are some fascinating ones to put on your to-do list.
What are the top hotels in Windsor?
If this will be your first visit to Windsor, book a room at DoubleTree by Hilton Burlington Vermont or Hilton Burlington Lake Champlain. Both offer comfy beds and are popular options with many travellers.
How far in advance should I book my Windsor holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to a year in advance. This is typically the cheapest time to book. If circumstances have left you booking late, discount tickets to Windsor will sometimes occur just a few weeks before departure.
What does an Expedia Windsor travel package include?
With Expedia, you can choose a combination of flights, car rentals and hotels to create your ideal Windsor travel package. Once you've made your booking, you can add on fun stuff like tours and activities. Don't forget — the more you bundle, the more you stand to save!
What should I know before booking a Windsor travel package?
So many places to travel to, so many things to see. With a travel package, you can cross more of them off your list. Bundle your hotels, flights and rental cars and get ready to save.
Can I choose my airline with a Windsor Expedia travel package?
Yes — that's the beauty of an Expedia travel package. You get to choose. We have more than 550 partner airlines worldwide, so you have options galore when creating your Windsor trip.

* 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.