Windsor Holidays

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    Save up to €185 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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    Plan, book, and manage your trip all in one place

Top hotels in Windsor

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 €148 per night from 7 Sept to 8 Sept
€148
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Nice place when I stayed there the Maine legislature was in session and around 10 o’clock at night many state reps checked into the hotel. Nothing fancy but clean and great staff perfect for business travel."

Reviewed on 6 Aug 2025

Maine Evergreen Hotel, Ascend Hotel Collection
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 €137 per night from 4 Sept to 5 Sept
€137
4 Sept - 5 Sept
includes taxes & fees
8.6/10 Excellent! (778 reviews)
"The beds were extremely comfortable. The facility is clean , and the staff is very friendly."

Reviewed on 3 Aug 2025

Holiday Inn Express & Suites Waterville - North by IHG
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 €139 per night from 11 Aug to 12 Aug
€139
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very Good! (437 reviews)
"Great front desk staff. Very clean and updated rooms."

Reviewed on 1 Aug 2025

The Elmwood
See all 658 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 holiday 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 holiday 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 holiday packages and you could land some great off-season deals.
How many days is enough for Windsor?
With a well-organised 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday 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 customised Windsor holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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, favourite 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 holiday 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.