Windsor Holidays

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Your Windsor Holiday

When you choose a Windsor holiday package, you can relax and enjoy your adventure to the fullest. Uncover the best things about this exciting city knowing that all your travel needs have been taken care of in advance. You'll want to take in the sights during your trip to Windsor. Don't miss leading attractions such as Mount Ascutney, Mt Ascutney State Park and Saint-Gaudens National Historic Site. Whoever you're taking a break with and whatever your bank balance, your ultimate Windsor holiday is just a few clicks away with Expedia.

Windsor Holiday

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, Quechee State Park and Harpoon Brewery

Our pick of the best Windsor Hotel Deals

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 AU$194 per night from 10 Aug to 11 Aug
AU$194
10 Aug - 11 Aug
includes taxes & fees
7/10 Good! (1,010 reviews)
"The hotel was really nice and everything was very Convient and safe . The location is great."

Reviewed on 17 Jul. 2025

White River Inn and Suites
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
Fully refundableReserve now, pay when you stay
The price is AU$144 per night from 10 Aug to 11 Aug
AU$144
10 Aug - 11 Aug
includes taxes & fees
6.4/10 (1,010 reviews)
"Great place for the price."

Reviewed on 27 Jul. 2025

Super 8 by Wyndham White River Junction
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$835 per night from 17 Aug to 18 Aug
AU$835
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (528 reviews)
"Really enjoyed our stay."

Reviewed on 18 Jul. 2025

Woodstock Inn & Resort
See all 2,579 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Windsor

Paradise Park

Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Paradise Park

Frequently asked questions

How much does a Windsor holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday to Windsor costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
To score cheap Windsor holiday packages, plan your trip outside of peak times like public holidays and major events. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Windsor?
With a well-organised schedule, you can easily visit the main Windsor sights in a handful of days. But if you want to discover hidden spots or take day trips, think about booking your Windsor holiday for longer.
Is it worth booking a holiday package to Windsor?
Windsor offers everything you need for an amazing escape. Begin your Windsor holiday on a high note by visiting major attractions like South Congregational Church.
How to find the best Windsor package deals?
Landing a cheap Windsor package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Windsor package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor holiday as a package?
You can enjoy significant savings on your next Windsor break by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Windsor?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor holiday.
How to plan a trip to Windsor?

  1. Pick your travel dates: The things you'd like to do in Windsor and your preferred season can help you decide when to get away.
  2. Budget wisely: Besides the price of your stay, you should factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Windsor.
  3. Determine how many days away: Start by listing all the attractions you'd like to get to in Windsor. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalised Windsor holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.