Windsor Holidays

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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

Windsor Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Màs Boutique Hotel

Màs Boutique Hotel

3 out of 5
Rome City Centre
per person
19 Jul - 24 Jul
found 3 hours ago
Return direct flight included
Singapore (SIN) to Rome (FCO)
9.2/10 Wonderful! (25 reviews)
Very clean and safe hotel with spacious rooms, despite the hotel itself being old and compact with a limited number of rooms. The staff is very nice, and the area is beautiful, lively, and fun.

Reviewed on 15 Jun, 2025

Hotel Locarno

Hotel Locarno

5 out of 5
Rome City Centre
Save 100% on your flight
per person
19 Jul - 24 Jul
found 3 hours ago
Return direct flight included
Singapore (SIN) to Rome (FCO)
9.6/10 Exceptional! (480 reviews)
One of the best hotels in Rome . Fabulous

Reviewed on 16 May, 2025

9Hotel Cesari

9Hotel Cesari

4 out of 5
Rome City Centre
per person
21 Jul - 26 Jul
found 1 hour ago
Return direct flight included
Singapore (SIN) to Rome (FCO)
9.2/10 Wonderful! (668 reviews)
This property is in a great location for site seeing. Located on a small square with several restaurants it was still very quiet once the windows were closed. The staff were all very friendly and helpful and our room was very comfortable. But the best part was the amazing rooftop bar where breakfast was served every morning. It was great for a place to unwind in the evening with your favorite drink. We couldn’t ask for a more beautiful place to hang out while in Rome!

Reviewed on 10 Jun, 2025

UNA HOTELS Trastevere Roma

UNA HOTELS Trastevere Roma

4 out of 5
Rome City Centre
per person
19 Jul - 24 Jul
found 3 hours ago
Return direct flight included
Singapore (SIN) to Rome (FCO)
9.4/10 Exceptional! (1,009 reviews)
Not what expected, room was very small.

Reviewed on 15 Jun, 2025

Maison Roma Piazza di Spagna | UNA Esperienze

Maison Roma Piazza di Spagna | UNA Esperienze

4 out of 5
Rome City Centre
per person
21 Jul - 26 Jul
found 1 hour ago
Return direct flight included
Singapore (SIN) to Rome (FCO)
9.4/10 Exceptional! (235 reviews)
The staff was incredibly helpful!

Reviewed on 14 Jun, 2025

Top hotels in Windsor

OTL Gouverneur Sherbrooke
OTL Gouverneur Sherbrooke
5 out of 5
3131 rue King Ouest, Sherbrooke, QC
Fully refundableReserve now, pay when you stay
The price is S$246 per night from 13 Jul to 14 Jul
S$246
13 Jul - 14 Jul
includes taxes & fees
9.6/10 Exceptional! (1,538 reviews)
"Tout était parfait! De l'accueil au déjeuner, la propreté, la literie, le confort de la chambre, le hall d'entrée majestueux! Parfait!!!"

Reviewed on 15 Jun, 2025

OTL Gouverneur Sherbrooke
Manoir des Sables Hôtel & Golf
Manoir des Sables Hôtel & Golf
4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundable
The price is S$158 per night from 24 Jun to 25 Jun
S$158
24 Jun - 25 Jun
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"The grounds are beautiful and extensive. Restaurant gave wonderful food. Staff so helpful."

Reviewed on 13 Jun, 2025

Manoir des Sables Hôtel & Golf
Grand Times Hotel Sherbrooke
Grand Times Hotel Sherbrooke
4 out of 5
1, rue Belvedere Sud, Sherbrooke, QC
Fully refundable
8.2/10 Very Good! (1,000 reviews)
"Location near the Lac du Nations, cleanliness, quiet, artwork, everything seemed new."

Reviewed on 5 Jun, 2025

Get rates
Grand Times Hotel Sherbrooke
See all 170 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 from S$1,409 on Expedia for your Windsor getaway. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
January, February and November are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy periods means you can typically find better prices on accommodation and flights.
How many days is enough for Windsor?
Generally, a handful of days is enough to visit the main sights during your Windsor holiday. However, if you want to have more time to relax or go on day tours, think about extending your itinerary.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our “Packages” tab. Then apply some filters, like “Property type” and “Popular locations,” to tailor the results to your exact needs. You can also sort by “Package discount” and discover offers that come with big savings. If you don’t find the perfect Windsor package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You’ll generally score a better deal than booking each component individually. And you’ll still get the freedom to create a customised Windsor holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Windsor?
If you’re planning a spontaneous Windsor holiday, browse our last-minute deals that can be booked up to a week before you go. Don’t want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor?

  1. Choose your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your hotel will likely be the biggest expense during your trip to Windsor.
  3. Decide how long to go for: Now that you’re up to speed on Windsor, you can figure out the ideal length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that’s left is to find 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.