Windsor Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Windsor Vacation Packages
Windsor Hotel Deals
The August House
494 King St Windsor NS
￥23,970
￥28,625 total
Sep 1 - Sep 2
includes taxes & fees
10/10 Exceptional! (202 reviews)
"This was a beautiful inn and so welcoming, right down to the personalized hand written welcome note that was waiting for us. Really enjoyed the breakfast in the morning as well. Would highly recommend staying here!"
Reviewed on Aug 16, 2026
Gateway to Annapolis Valley | Windsor Studio Suite
Windsor NS
￥14,055
￥24,270 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (4 reviews)
"Everything about this property was as described - and its location was perfect for us! Restaurants and pubs were an easy 5 minute walk. Highly recommend!"
Reviewed on Aug 7, 2026
Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor NS
￥17,155
￥27,804 total
Aug 19 - Aug 20
includes taxes & fees
10/10 Exceptional! (1 review)
"The accommodation was impeccably clean and well appointed with everything a traveller would require. Lots of coffee, close distance to amenities, shops, restaurants and more. I would certainly return and hopefully, stay longer !"
Reviewed on Aug 10, 2026
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 studying the exhibits at Haliburton House Museum in Windsor. You can enjoy the wineries while in the area.
West Hants Historical Society
7.0/10 (4 reviews)
You can spend time browsing the exhibits at West Hants Historical Society in Windsor. You can enjoy the wineries while in the area.
Trecothic Creek and Windsor Railway
You can spend an afternoon studying the exhibits at Trecothic Creek and Windsor Railway during your travels in Windsor. You can enjoy the wineries while in the area.
Windsor Hockey Heritage Centre
9.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Windsor Hockey Heritage Centre in Windsor. You can enjoy the wineries while in the area.
Mermaid Theatre of Nova Scotia
7.0/10 (2 reviews)
You can enjoy a show at Mermaid Theatre of Nova Scotia on your trip to Windsor. You can enjoy the wineries while in the area.
Fountain Cultural & Performing Arts Centre
Enjoy an outing to Fountain Cultural & Performing Arts Centre during your stay in Windsor. Take in the museums and countryside in the area.
Shand House Museum
10.0/10 (1 review)
You can spend time studying the exhibits at Shand House Museum during your travels in Windsor. You can enjoy the wineries while in the area.
Fort Edward National Historic Site
8.8/10 (3 reviews)
You can find out about the history of Windsor when you stop by Fort Edward National Historic Site. You can enjoy the wineries while in the area.
Frequently asked questions
How much does a Windsor vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation packages. Traveling in quieter months means you can typically find better prices on hotels and flights.
How many days is enough for Windsor?
For your Windsor vacation, 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 vacation package to Windsor?
It's no wonder a Windsor vacation is on the must-do list of many travelers. 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 vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize 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 vacation 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?
- 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.
- 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.
- 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.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Windsor vacation 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.
