Windsor Vacations from $641

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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.
Surfside Inn
Lux Exec Home HFX Waterfront Pool Hot Tub
Brier Island Lodge
Chateau Bedford, Trademark Collection by Wyndham
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
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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! (120 reviews)
"Very clean, modern and charming. I appreciated the small touches, including the Nespresso and the white noise machine. (If all the doors could be oiled it would make it even better as the quarters are pretty tightly packed so you hear everything)"

Reviewed on Aug 12, 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
Old Orchard Inn & Spa

Old Orchard Inn & Spa

4 out of 5
153 Greenwich Rd. South, Exit 11, Highway 101, Wolfville Ridge, NS
$169 nightly
The price is $192 total per night from Sep 18 to Sep 19
$192 total
Sep 18 - Sep 19
Total includes taxes and fees
8.2/10 Very Good! (1,008 reviews)
Beautiful
"We loved the hotel and the restaurant and the area. Great wineries and beautiful place overall. The food in the restaurant was excellent as was the service."

Reviewed on Aug 20, 2025

Old Orchard Inn & Spa
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.

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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 $641 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.