Title: Windsor Holidays 2025 | Expedia.co.uk [Hotels in Windsor](https://expedia.co.uk/Windsor-Hotels.d7881.Travel-Guide-Hotels)[Holiday Rentals in Windsor](https://expedia.co.uk/Windsor-Holiday-Rentals.d7881.Travel-Guide-HolidayRentals)[Windsor Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windsor.d7881.Car-Hire-Guide) ![](https://images.trvl-media.com/place/7881/9675231b-9d1e-4af8-9ac0-4a4684345ff1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Holidays from £1,438 ## Book a Hotel + Flight or Car together to unlock savings Photo by mike dobias - ## Plan, book, travel with confidence - ### Better together Save up to £335 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### 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](https://www.expedia.co.uk/Mount-Ascutney-Windsor.d553248621532666931.Attraction), [Blow-Me-Down Bridge](https://www.expedia.co.uk/Blow-Me-Down-Bridge-Cornish.d553248621532666969.Attraction) and [Mt Ascutney State Park](https://www.expedia.co.uk/Mt-Ascutney-State-Park-Vermont.d6175264.Attraction). 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. ![Sinclair Inn Bed and Breakfast](https://images.trvl-media.com/lodging/91000000/90830000/90821100/90821033/c85ac41d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sinclair Inn Bed and Breakfast £1,438 per person 27 Dec - 3 Jan found 24 hours ago Return direct flight included London (LHR) to Springfield (VSF) 10/10 Exceptional! (99 reviews) Highly recommend staying here. I will stay here again if I’m ever planning to return to Vermont. The customer service is top notch and we really enjoyed the locally sourced homemade breakfast too. Everything was a dreamy bed and breakfast. Reviewed on 2 Nov 2025 [](https://expedia.co.uk/go/package/search/FlightHotel/2025-12-27/2026-01-03/?FromAirport=LHR&Destination=VSF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=90821033&paandie=true&dealMarker=OX2bllZ7n7fY0CIeHXCOjZ0LAu32YN0ye48DjSRGfn2YRrR7jd78159AucNcmTj2) ## 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](https://www.expedia.co.uk/Mt-Ascutney-State-Park-Vermont.d6175264.Attraction), [Harpoon Brewery](https://www.expedia.co.uk/Harpoon-Brewery-Windsor.d553248635975913439.Attraction) and [Quechee State Park](https://www.expedia.co.uk/Quechee-State-Park-Quechee.d553248621532667673.Attraction) | ## Top hotels in Windsor ![Fat Sheep Farm & Cabins](https://images.trvl-media.com/lodging/46000000/45550000/45547000/45546970/03f7a10c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fat Sheep Farm & Cabins 122 Best Rd, Windsor, VT 9.6/10 Exceptional! (11 reviews) An absolutely stunning property! The cabin was clean, well stocked and perfectly located to see the gorgeous sunrise. So very grateful for our quick trip at Fat Sheep Farm. Looking forward to returning! Reviewed on 6 May 2025 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=45546970&PinnedHotelID=45546970&HadPinnedHotel=true®ionId=7881) [](https://expedia.co.uk/Hotel-Search?startDate=22%2F11%2F2025&endDate=23%2F11%2F2025&selected=45546970&PinnedHotelID=45546970&HadPinnedHotel=true®ionId=7881) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/403a8548_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington Mountain Lodge, Tapestry Collection by Hilton 2617 Killington Rd, Killington, VT Fully refundableReserve now, pay when you stay £109 16 Nov - 17 Nov includes taxes & fees 7.2/10 Good! (1,000 reviews) very nice place Reviewed on 22 Oct 2025 [](https://expedia.co.uk/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=7881) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/6bca8eff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodstock Inn & Resort Fourteen The Green, Woodstock, VT £308 3 Dec - 4 Dec includes taxes & fees 9.2/10 Wonderful! (546 reviews) I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn Reviewed on 4 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=03%2F12%2F2025&endDate=04%2F12%2F2025&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=7881) [See all 2,587 properties in Windsor](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F11%2F2025&endDate=10%2F11%2F2025®ionId=7881) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Explore a world of travel with Expedia \* 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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)