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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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Maine Evergreen Hotel, Ascend Hotel Collection
Maine Evergreen Hotel, Ascend Hotel Collection
2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is NT$4,902 per night from Jul 6 to Jul 7
NT$4,902
NT$5,343 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"YOUR BAR AREA."

Reviewed on 2025/7/2

Maine Evergreen Hotel, Ascend Hotel Collection
Fireside Inn & Suites Waterville
Fireside Inn & Suites Waterville
2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is NT$4,557 per night from Jul 7 to Jul 8
NT$4,557
NT$4,967 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The staff are very friendly, and they support one another. The breakfast is nicely laid out, and you had an option of preparing a bag to take with you. On a couple of days we prepared a lunch of bagel and cream cheese to take with us. This is an older hotel, but will maintained, and reminiscent of ..."

Reviewed on 2025/6/22

Fireside Inn & Suites Waterville
The Elmwood
The Elmwood
2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is NT$4,296 per night from Jul 7 to Jul 8
NT$4,296
NT$4,683 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (410 reviews)
"Continental breakfast was good. Location was convenient. Value could have been better …"

Reviewed on 2025/6/27

The Elmwood
See all 672 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.

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices on Expedia for your Windsor break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
You're likely to find reduced prices and greater availability in January, February and March. Browse our cheap Windsor vacation packages and you could land some great off-season deals.
How many days is enough for Windsor?
With a well-organized schedule, you can easily tick off the most popular Windsor attractions 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.
How to find the best Windsor package deals?
Use Expedia's filters to find some unbeatable Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Windsor package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Windsor vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Windsor?
Enjoy amazing 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 break.
How to plan a trip to Windsor?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Windsor.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Windsor.
  3. Decide your trip length: Think about how long you'd like to spend discovering Windsor. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Windsor vacation package that brings all your bookings together.

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