Windsor Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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

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 S$217 per night from 1 Sept to 2 Sept
S$217
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Great little hotel. A bit dated but the hotel is clean and quiet and the breakfast was wonderful. Would stay again and recommend to family and friends."

Reviewed on 19 Aug, 2025

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 S$204 per night from 24 Aug to 25 Aug
S$204
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (999 reviews)
Exceptional
"Everyone was so pleasant and pet friendly specially where I have a Service Dog."

Reviewed on 19 Aug, 2025

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 S$209 per night from 24 Aug to 25 Aug
S$209
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (455 reviews)
"Amanda at check in was fantastic! Room recently refurbished, clean, and comfortable."

Reviewed on 16 Aug, 2025

The Elmwood
See all 653 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.