Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Windsor Vacation Packages

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 NT$3,407 per night from Aug 10 to Aug 11
NT$3,407
NT$3,748 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (1,004 reviews)
"Going in was a warm feeling and staff was friendly. Our room door didnt close like it should and we had to close it roughly which made it for an unnecsary noise to us and others next to us."

Reviewed on 2025/8/3

White River Inn and Suites
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 NT$3,927 per night from Aug 10 to Aug 11
NT$3,927
NT$4,910 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"Breakfast could be better."

Reviewed on 2025/8/5

Fireside Inn & Suites West Lebanon
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NT$12,254 per night from Sep 1 to Sep 2
NT$12,254
NT$14,798 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (530 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 2025/7/30

Woodstock Inn & Resort
See all 2,575 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.

Discover the most popular places to visit in Windsor

The Sustainable Farmer

Enjoy an outing to The Sustainable Farmer during your stay in Windsor. Wander the riverfront in this quaint area.

The Sustainable Farmer

Paradise Park

4/5(4 reviews)

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

Paradise Park

Old Constitution House

You can learn about the history of Windsor with a visit to Old Constitution House. Wander the riverfront in this quaint area.

Old Constitution House

Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But how much your vacation 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 vacation 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-organized 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 vacation for longer.
Is it worth booking a vacation package to Windsor?
Windsor offers everything you need for an amazing escape. Begin your Windsor vacation 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," "Traveler 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation 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 vacation.
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 personalized Windsor vacation package.

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