Windsor Holidays from £963
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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.
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
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is £112 per night from 19 May to 20 May
£112
19 May - 20 May
includes taxes & fees
7.4/10 Good! (1,004 reviews)
Great experience as always. Great place to be close to the slopes, especially if you have your pup with you.
Reviewed on 26 Apr 2026
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
The price is £110 per night from 10 May to 11 May
£110
10 May - 11 May
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Dining was a huge disappointment at night. Probably because we were thr only ones interested in attending dinner.
Reviewed on 5 May 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is £291 per night from 25 May to 26 May
£291
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (575 reviews)
Everything was excellent
Reviewed on 5 May 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.
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* 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.
