Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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Top hotels in Windsor

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 2.818.122 ₫ per night from 24 Aug to 25 Aug
2.818.122 ₫
3.099.935 ₫ total
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (1,002 reviews)
"The staff was the best part of this stay. They were friendly and welcoming. The room was very spacious and comfortable for the price."

Reviewed on 13 Aug 2025

White River Inn and Suites
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is 10.762.017 ₫ per night from 1 Sept to 2 Sept
10.762.017 ₫
12.995.990 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul 2025

Woodstock Inn & Resort
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road, West Lebanon, NH
Fully refundableReserve now, pay when you stay
The price is 3.845.183 ₫ per night from 7 Sept to 8 Sept
3.845.183 ₫
4.744.318 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"This is a really neat hotel with nice amenities but it is also old so it has old plumbing and old ventilation"

Reviewed on 18 Aug 2025

Fireside Inn & Suites West Lebanon
See all 2,574 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.

Popular places to visit

Harpoon Brewery

You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forests or discover the area's mountain views.

Harpoon Brewery

American Precision Museum

You can spend time exploring the galleries in American Precision Museum during your travels in Windsor. Wander the riverfront in this quaint area.

American Precision Museum

Path of Life Garden

Explore the great outdoors at Path of Life Garden, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Path of Life Garden

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.