Windsor Vacations from $641

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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

Surfside Inn

3 out of 5
Price was $829, price is now $641 per person
$641
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Halifax (YHZ)
8.8/10 Excellent! (320 reviews)
Welcoming staff and clean, quiet property, minutes away from a beautiful sandy beach where you can swim. Property has an old inn charm with vintage decoration. At night, you can hear the waves if you have a water facing room!

Reviewed on Aug 18, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Save 100% on your flight
Price was $2,029, price is now $1,135 per person
$1,135
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on Jul 25, 2025

Brier Island Lodge

Brier Island Lodge

3 out of 5
Price was $1,121, price is now $885 per person
$885
per person
Oct 11 - Oct 18
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Halifax (YHZ)
8.2/10 Very Good! (377 reviews)
Spectacular views from the dining room . Food was excellent and staff was most helpful and accommodating.

Reviewed on Aug 18, 2025

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was $1,244, price is now $991 per person
$991
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.2/10 Wonderful! (1,983 reviews)
Clean and comfortable. Well located to the highway. Approximately 20 minutes to the Halifax boardwalk. Rooms well appointed with fridge and microwave.

Reviewed on Aug 18, 2025

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was $841, price is now $679 per person
$679
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
7.4/10 Good! (1,018 reviews)
Loved the location, everything was clean, and staff were very friendly. Love that there was a restaurant and bar right in the motel, with VLTs. Eill definitely stay again.

Reviewed on Aug 19, 2025

Don't see what you're looking for?
See all available trips from Columbus to Windsor
View all trips

Discover the most popular places to visit in Windsor

Haliburton House Museum

You can spend time studying the exhibits at Haliburton House Museum in Windsor. You can enjoy the wineries while in the area.

Haliburton House Museum

Mermaid Theatre of Nova Scotia

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.

Mermaid Theatre of Nova Scotia

Shand House Museum

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.

Shand House Museum

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

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
$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
See all 126 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.