Windsor Vacation Packages

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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.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Liscombe Lodge Resort and Conference Centre

Liscombe Lodge Resort and Conference Centre

2.5 out of 5
per person
Sep 15 - Sep 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (255 reviews)
Food was spectacular and we loved the pool, farm animals, kayaking and fishing.

Reviewed on Aug. 4, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on Jul. 25, 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
7.8/10 Good! (4,300 reviews)
The hotel was nice and great location for activities downtown. The parking however is quite a walk and $60 for 2 nights on top of 257 pre night was a bit pricy.

Reviewed on Aug. 9, 2025

Brier Island Lodge

Brier Island Lodge

3 out of 5
per person
Oct 11 - Oct 18
found 4 hours ago
Roundtrip flight included
Calgary (YYC) to Halifax (YHZ)
8.2/10 Very Good! (377 reviews)
Really enjoyed our stay. Very nice staff! Facilities are great, however, an upgrade on the mattresses is in order.

Reviewed on Aug. 8, 2025

South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.2/10 Very Good! (665 reviews)
We rented a room with a kitchenette. It had nearly everything we would need to cook with - which was lovely. Bed was comfortable. Room was clean. Tv was nice size.plenty of towels and soap. We will rent from here again.

Reviewed on Aug. 9, 2025

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

The August House

The August House

3.5 out of 5
494 King St, Windsor, NS
The price is CA $235 per night from Sep 4 to Sep 5
CA $235
CA $287 total
Sep 4 - Sep 5
includes taxes & fees
9.8/10 Exceptional! (116 reviews)
"Great stay, clean room, welcoming breakfast"

Reviewed on Aug. 7, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Aug 14 to Aug 15
CA $215
CA $267 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Food is great"

Reviewed on Aug. 8, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

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.

Trecothic Creek and Windsor Railway

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $390 on Expedia for your Windsor escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're looking to book a cheap Windsor vacation package, consider visiting in January, February and November. You'll typically find better prices on flights and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Windsor?
Usually, a handful of days is ideal for a Windsor vacation. With a well-planned itinerary, you can visit all the popular sights such as Mermaid Theatre of Nova Scotia, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Windsor?
It's easy to see why a Windsor vacation is on the to-do list of many travellers. Leading attractions like Mermaid Theatre of Nova Scotia are just the start of things to see and do here.
How to find the best Windsor package deals?
Use Expedia's filter tool to find some unbeatable Windsor package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Windsor package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Windsor vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're considering a spur-of-the-moment Windsor adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred time of year and the activities available will also help you decide when to escape to Windsor.
  2. Set a budget: Consider expenses such as flights, meals and transportation when calculating how much to set aside for your trip to Windsor. Then, select a property that suits your budget, whether that's a wallet-friendly option or a swankier getaway.
  3. Work out your trip length: Consider how long you'd like to spend exploring Windsor. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Windsor vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.