Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to Rp173.195 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Windsor

The August House
The August House
3.5 out of 5
494 King St, Windsor, NS
9.8/10 Exceptional! (102 reviews)
"The August House is stunning! It’s a great home base for exploring the wineries and other sights in the valley. Several nice restaurants in walking distance, too."

Reviewed on 17 Jun 2025

Get rates
The August House
Meander In Bed and Breakfast
Meander In Bed and Breakfast
2 out of 5
153 Albert St, Windsor, NS
Get rates
Meander In Bed and Breakfast
Old Orchard Inn & Spa
Old Orchard Inn & Spa
4 out of 5
153 Greenwich Rd. South, Exit 11, Highway 101, Wolfville Ridge, NS
Fully refundableReserve now, pay when you stay
The price is Rp2.728.248 per night from 8 Jul to 9 Jul
Rp2.728.248
Rp3.365.157 total
8 Jul - 9 Jul
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Beautiful view,with rooms in the back. Renovations are still occurring, but will be very nice when done.New restaurant, and new menus. Bonus."

Reviewed on 20 Jun 2025

Old Orchard Inn & Spa
See all 115 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 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.