Windsor Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 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

Holiday Inn Express & Suites Waterville - North by IHG
Holiday Inn Express & Suites Waterville - North by IHG
2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
The price is AED 437 per night from Apr 27 to Apr 28
AED 437
AED 476 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (727 reviews)
"The suite was lovely!"

Reviewed on 17 April 2025

Holiday Inn Express & Suites Waterville - North by IHG
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 AED 511 per night from Apr 21 to Apr 22
AED 511
AED 557 total
includes taxes & fees
21 Apr - 22 Apr
9/10 Wonderful! (1,003 reviews)
"The room and beds were a lot smaller than I thought they would be. It was clean and other than being small the beds were comfy. The employees are great, especially housekeeping."

Reviewed on 18 April 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Senator Inn & Spa
Senator Inn & Spa
3 out of 5
284 Western Ave, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is AED 463 per night from Apr 21 to Apr 22
AED 463
AED 504 total
includes taxes & fees
21 Apr - 22 Apr
7.6/10 Good! (1,000 reviews)
"Me and my kids had an amazing night staying in a suite just to have a little get away. They didn't want to leave. The only thing i would say is i wish the pool was av little warmer"

Reviewed on 13 April 2025

Senator Inn & Spa
See all 644 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 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.