Windsor Holidays from £1,125
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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.
Top Windsor Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
1846 Inn and Tavern
£1,313
per person
26 Dec - 31 Dec
found 22 hours ago
Return direct flight included
London (LON) to Springfield (VSF)
10/10 Exceptional! (1 review)
We went for a girls trip for one night! Everything was amazing from check in to check out! We felt like we were greeting and taking care of our stay. The food is amazing the atmosphere is fantastic and can’t wait till next year!!!!
Reviewed on 21 Sept 2026
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
Fat Sheep Farm & Cabins
122 Best Rd Windsor VT
£151
3 Nov - 4 Nov
includes taxes & fees
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"
Reviewed on 5 Jan 2026
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
£106
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (1,008 reviews)
"Scratching in the walls behind the bed and a terrible smell. Likely dead animal in the walls"
Reviewed on 9 Oct 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
£117
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"We were most appreciative of the help with our baggage by the staff since there were steps but no elevator. The staff were very friendly as well. We enjoyed a delicious meal right there in the still on the Mountain. Unfortunately there was a floor above us and the footsteps were heard felt like the ..."
Reviewed on 10 Oct 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
Brownsville Trail
9.4/10 (3 reviews)
This challenging 5.2-mile trail rewards hikers with panoramic views and the historic Norcross Quarry from the early 1900s. Pack water and wear sturdy boots for the 2,395-foot ascent through Vermont's forests.
Paradise Park
8.8/10 (8 reviews)
Paradise Park offers diverse ecosystems around Lake Runnemede, with well-maintained trails through forests and meadows. Observe abundant wildlife including birds, turtles, and beavers in this peaceful natural sanctuary.
Harpoon Brewery
9.4/10 (23 reviews)
This working brewery offers a unique tasting experience with fresh craft beers and handmade pretzels. Enjoy the communal atmosphere in the taproom overlooking brewing operations or relax in the outdoor beer garden.
American Precision Museum
10.0/10 (2 reviews)
Housed in the historic 1846 Robbins & Lawrence Armoury, this museum showcases America's largest collection of significant machine tools. Interactive exhibits highlight how precision manufacturing shaped our industrial heritage.
Ascutney Park
Vermont's first state park offers 12+ miles of trails through former quarries and historic homesteads. Drive the 3.7-mile auto road for panoramic views of the Connecticut River Valley without the summit hike.
Weathersfield Proctor Library
This community-centered library offers a welcoming hub for book lovers and local engagement. Browse their diverse collection or join one of their regular educational programmes in this Ascutney gathering place.
Windsor Public Library
This historic library has served as Windsor's community hub since 1882, offering diverse collections for all ages. Browse books, use free Wi-Fi, or join one of their engaging programmes.
Silo Distillery
You can take time to visit Silo Distillery during your travels to Windsor. Wander the forests or discover the area's mountain views.
Frequently asked questions
How much does a Windsor travel package cost?
Discover the best of Windsor from as low as £1,125. 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.
