Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windsor

The August House

The August House

3.5 out of 5
494 King St, Windsor, NS
9.8/10 Exceptional! (111 reviews)
"The short stay at TheAugustHoyse was amazing and we cant wait to visit again."

Reviewed on 19 Jul 2025

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The August House
Meander In Bed and Breakfast

Meander In Bed and Breakfast

2 out of 5
153 Albert St, Windsor, NS
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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 4.325.097 ₫ per night from 5 Aug to 6 Aug
4.325.097 ₫
5.334.790 ₫ total
5 Aug - 6 Aug
includes taxes & fees
8.2/10 Very Good! (1,014 reviews)
"Limited staffing for restaurant making for a long wait time for breakfast and service overall."

Reviewed on 30 Jul 2025

Old Orchard Inn & Spa
See all 122 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.

Popular places to visit

Trecothic Creek and Windsor Railway

You can spend an afternoon studying the exhibits at Trecothic Creek and Windsor Railway during your trip to Windsor. You can enjoy the wineries while in the area.

Trecothic Creek and Windsor Railway

Fort Edward National Historic Site

You can find out about the history of Windsor with a stop at Fort Edward National Historic Site. You can enjoy the wineries while in the area.

Fort Edward National Historic Site

Shand House Museum

You can spend time exploring the galleries in Shand House Museum during your travels in Windsor. You can enjoy the wineries while in the area.

Shand House Museum

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.