Windsor Vacations from $380

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Your Windsor Vacation

Create a custom vacation package to Windsor and start looking forward to your next great adventure. Consider staying in the neighborhood of Gaspereau, which is great for watersports and views, for a real taste of this unique city. If your trip to Windsor includes some sightseeing, check out much-loved attractions like Ski Martock, Avon River Heritage Society Museum and Mermaid Theatre of Nova Scotia. Whatever your travel plans or budget, organizing a tailored Windsor vacation is easy with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
The Barrington Hotel
Lux Exec Home HFX Waterfront Pool Hot Tub
The Sutton Place Hotel Halifax
Cambridge Suites Hotel
The Fourth Lock Bed & Breakfast
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Discover the most popular places to visit in Windsor

Windsor Hotel Deals

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 Jun 17, 2025

The August House
Meander In Bed and Breakfast
Meander In Bed and Breakfast
2 out of 5
153 Albert St, Windsor, NS
Meander In Bed and Breakfast
Micro Boutique Living Wolfville
Micro Boutique Living Wolfville
3.5 out of 5
336 Main Street, Wolfville, NS
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $127 total per night from Jul 6 to Jul 7
$127 total
Jul 6 - Jul 7
Total includes taxes and fees
8.8/10 Excellent! (955 reviews)
"Awesome location and hotel -definately will be back"

Reviewed on Jun 30, 2025

Micro Boutique Living Wolfville
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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
Canadian dollars
Population
3,900
Max Temp Winter
35ºF
Max Temp Summer
70ºF
Top Sights
Ski Martock, Smileys Provincial Park and West Hants Historical Society

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Frequently asked questions

How much does a Windsor vacation package cost?
You can pick up a vacation package to this top destination from $380 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, October and December are the best times to look for cheap Windsor vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Windsor?
Generally, a few days is enough for a Windsor vacation. With a carefully crafted itinerary, you can go to all the popular attractions such as Windsor Hockey Heritage Centre, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Windsor?
Windsor has everything you need for an unforgettable escape. Get your Windsor vacation off to a flying start by checking out popular attractions like Mermaid Theatre of Nova Scotia.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Secure your dream trip to Windsor with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday --- we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.