Windsor Holidays

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Windsor Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
per person
9 Jun - 12 Jun
found 11 hours ago
Return flight included
San Francisco (SFO) to Los Angeles (LAX)
8.4/10 Very Good! (1,001 reviews)
Great quiet location.

Reviewed on 28 Mar,2025

Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Manhattan
Save 100% on your flight
per person
11 May - 16 May
found 7 hours ago
Return flight included
Boston (BOS) to New York (JFK)
7.6/10 Good! (670 reviews)
It is good hotel but definitely need some update as it seem outdated and my shower only hat boiling water. Otherwise the staff were amazing.

Reviewed on 21 Mar,2025

Regent Santa Monica Beach

Regent Santa Monica Beach

5 out of 5
Downtown Santa Monica
Save 100% on your flight
per person
9 Jun - 12 Jun
found 11 hours ago
Return flight included
San Francisco (SFO) to Los Angeles (LAX)
10/10 Exceptional! (2 reviews)
Beautiful resort, easy access to beach, all staff was superb in service. Had a weekend birthday celebration and the staff made sure all our guests were greeted and cared for in a most welcoming way. Thank you to Myra Castillo and all the great staff for a wonderful and memorable stay. Highly recommend it.

Reviewed on 11 Oct,2024

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
11 May - 16 May
found 7 hours ago
Return flight included
Boston (BOS) to New York (JFK)
8.2/10 Very Good! (2,806 reviews)
My partner and I had a good stay at the hotel. Rooms are very small, but this is to be expected in NYC. Very nice modern touches throughout the property and convenient lockers for your luggage can be used before/after check out. A couple things that could’ve been better: -our water glasses, for drinking, were not changed once over out 4 day/3 night stay. Definitely expected new glasses to be provided each day. -more towels are always a plus -better lighting in the sink area, as partner had difficulty applying makeup. -it was a bit confusing trying to make our way up to the rooftop as it was unmarked. Other than those minor changes, good hotel. The area is fantastic. Very walkable - especially to lots of good food/drink areas in SOHO & Chinatown. I would stay at the hotel again.

Reviewed on 28 Mar,2025

33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
per person
11 May - 16 May
found 7 hours ago
Return flight included
Boston (BOS) to New York (JFK)
9.2/10 Wonderful! (707 reviews)
Very convenient location at seaport. Will come back with family.

Reviewed on 14 Mar,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$239 per night from 6 Apr to 7 Apr
S$239
includes taxes & fees
6 Apr - 7 Apr
9.6/10 Exceptional! (1,487 reviews)
"Amazing smell in the hotel, the staff is really nice 👍"

Reviewed on 23 Mar,2025

OTL Gouverneur Sherbrooke
Comfort Inn Sherbrooke
Comfort Inn Sherbrooke
2.5 out of 5
4295 boul. Bourque, Sherbrooke, QC
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 6 Apr to 7 Apr
S$129
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (1,003 reviews)
"very good for the cost. FYI no elevator to second floor so keep that in mind."

Reviewed on 22 Mar,2025

Comfort Inn Sherbrooke
Manoir des Sables Hôtel & Golf
Manoir des Sables Hôtel & Golf
4 out of 5
90 Des Jardins Ave., Orford, QC
Fully refundableReserve now, pay when you stay
The price is S$140 per night from 6 Apr to 7 Apr
S$140
includes taxes & fees
6 Apr - 7 Apr
8/10 Very Good! (1,002 reviews)
Hotel correct sans plus
"Hotel correct et bon service , les spas sont tres propre, le seul hic est que les matelas sont tres dur."

Reviewed on 26 Mar,2025

Manoir des Sables Hôtel & Golf
See all 176 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$869 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.