Windsor Holidays from £379

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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.

The Latest Windsor Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
8/10 Very Good! (206 reviews)
Loved the location for this ski in ski out. Nice to look out the balcony and be right in the middle of the action. The sofa bed was uncomfortable with springs popping up all over. The back door didn't lock and the window handle was broken . There was a light bulb that was out and not all the outlets worked. The tv situation was a nightmare with one tv all snowy and the other one whose remote was missing the select button and could not choose a channel. The location was great but would not choose this room again .

Reviewed on 19 Feb 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
10/10 Exceptional! (5 reviews)
Great location , friendly and knowledgeable staff !

Reviewed on 14 Jun 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (759 reviews)
Surprisingly my room had a fireplace and a patio with a lovely river view. Get the river view! I didn’t want to leave after one night, so just before checkout I asked for another night.

Reviewed on 20 Jun 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (729 reviews)
The lady at the front desk was so accommodated and welcoming. Definitely one of the reasons that they keep me coming back.

Reviewed on 18 Jun 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
8.6/10 Excellent! (193 reviews)
Outdoor pool was great !

Reviewed on 2 Mar 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
21 Jul - 23 Jul
found 1 day ago
Return flight included
New York (NYC) to Springfield (VSF)
9.2/10 Wonderful! (519 reviews)
Super weekend- elegant and relaxed.

Reviewed on 8 May 2025

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

Our pick of the best Windsor Hotel Deals

Align Inn Vermont
Align Inn Vermont
2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
9.2/10 Wonderful! (1,009 reviews)
"Great staff, good location a short walk from the historic center. A bit expensive."

Reviewed on 21 Jun 2025

Align Inn Vermont
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (519 reviews)
Stunning
"Always a stunning stay in Woodstock!"

Reviewed on 2 Jun 2025

Woodstock Inn & Resort
Super 8 by Wyndham White River Junction
Super 8 by Wyndham White River Junction
2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the ...
6.2/10 (1,005 reviews)
"The location is very easy to access close enough to restaurants and other necessities nearby in White River junction. The staff was excellent very friendly and helpful. The building itself needs some maintenance in terms of structural and cosmetic attention. The room was clean the bed was comfortable ..."

Reviewed on 17 Jun 2025

Super 8 by Wyndham White River Junction
See all 2,603 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 £379. 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.