Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to NT$5,067 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    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$4,637 per night from Jun 26 to Jun 27
NT$4,637
NT$5,054 total
Jun 26 - Jun 27
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Great"

Reviewed on 2025/6/21

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$4,187 per night from Jun 29 to Jun 30
NT$4,187
NT$4,564 total
Jun 29 - Jun 30
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"I love the fact that they are pet friendly and have a wonderful hot tub. Our room was spacious and very clean. The Governors restaurant was very good!! Will definitely stay here again!"

Reviewed on 2025/6/19

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$4,105 per night from Jun 26 to Jun 27
NT$4,105
NT$4,474 total
Jun 26 - Jun 27
includes taxes & fees
8.6/10 Excellent! (409 reviews)
"Newly remodeled rooms were clean and comfortable. Staff were very friendly."

Reviewed on 2025/6/18

The Elmwood
See all 671 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.