Windsor Holidays

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    Save up to S$1,300 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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Top hotels in Windsor

The August House

The August House

3.5 out of 5
494 King St Windsor NS
The price is S$218 per night from 18 Nov to 19 Nov
S$218
18 Nov - 19 Nov
includes taxes & fees
The August House
Old Orchard Inn

Old Orchard Inn

4 out of 5
153 Greenwich Rd. South Wolfville Ridge NS
Fully refundableReserve now, pay when you stay
The price is S$235 per night from 15 Nov to 16 Nov
S$235
15 Nov - 16 Nov
includes taxes & fees
8.6/10 Excellent! (1,066 reviews)
"Thank you :)"

Reviewed on 11 Nov, 2026

Old Orchard Inn
Slumber Inn

Slumber Inn

3.5 out of 5
5534 Prospect Road New Minas NS
Fully refundableReserve now, pay when you stay
The price is S$170 per night from 13 Dec to 14 Dec
S$170
13 Dec - 14 Dec
includes taxes & fees
Slumber Inn
See all 178 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.

Stay near popular Windsor attractions

Haliburton House Museum

9.0/10 (2 reviews)
You can spend time browsing the exhibits at Haliburton House Museum in Windsor. You can enjoy the wineries while in the area.
See properties

Frequently asked questions

How much does a Windsor holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Windsor costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Windsor?
January, February and November are great times to look for cheap Windsor holiday packages. Travelling in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for Windsor?
For your Windsor holiday, a handful of days will be enough to explore the best spots. Be sure to stop by West Hants Historical Society — it's one of the leading attractions in this destination. If you want more activities, think about basing yourself here and setting off on some day tours from Windsor.
Is it worth booking a holiday package to Windsor?
It's no wonder a Windsor holiday is on the must-do list of many travellers. Major attractions like Mermaid Theatre of Nova Scotia are just the beginning of things to keep you busy here.
How to find the best Windsor package deals?
Use Expedia's filters to find some tempting Windsor package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Windsor package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customise your Windsor getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Windsor?
If you've got your Windsor travel dates finalized, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred season and the type of activities available will also help you decide when to escape to Windsor.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your hotel will probably be the biggest expense during your trip to Windsor.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Windsor. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose 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.