Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
8.2/10 Very Good! (620 reviews)
I liked the room. It was clean. What I didn’t like was the dog barking at night next door. Then on Friday morning, there was consruction early in the morning next door. Very annoying. If you knew you are having construction done, why book a room right near tge site. 😳

Reviewed on Jul. 5, 2025

The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

5 out of 5
Downtown Halifax
Save 100% on your flight
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.6/10 Exceptional! (1,682 reviews)
Always provides a excellent location when visiting Halifax

Reviewed on Jul. 4, 2025

Surfside Inn

Surfside Inn

3 out of 5
Save 100% on your flight
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.8/10 Excellent! (295 reviews)
Very cute. Perfect for 3 ladies on a girls weekend.

Reviewed on Jul. 1, 2025

Liscombe Lodge Resort and Conference Centre

Liscombe Lodge Resort and Conference Centre

2.5 out of 5
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
8.2/10 Very Good! (237 reviews)
I’ve been coming to the lodge for 30 yrs, the chalets and cabins are looking tired and it’s a large property to keep on top of

Reviewed on Jun. 30, 2025

Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

3 out of 5
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (1,305 reviews)
It was a great time spent

Reviewed on Jul. 5, 2025

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

The August House
The August House
3.5 out of 5
494 King St, Windsor, NS
The price is CA $230 per night from Jul 6 to Jul 7
CA $230
CA $281 total
Jul 6 - Jul 7
includes taxes & fees
9.8/10 Exceptional! (103 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
Get rates
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
The price is CA $143 per night from Jul 20 to Jul 21
CA $143
CA $163 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (961 reviews)
"Very convenient. Walking distance to all areas. Easy check in and out"

Reviewed on Jul. 2, 2025

Micro Boutique Living Wolfville
See all 117 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 $702 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.