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.
Bridgetown Motor Inn

Bridgetown Motor Inn

CA $441
per person
Nov 27 - Nov 30
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
7.4/10 Good! (283 reviews)
It’s all good good place

Reviewed on Oct 12, 2026

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

CA $1,422
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.8/10 Exceptional! (8 reviews)
Everything was unique especially the automated system. Enjoyed the spa. We had some difficulty using the living room tv. Could not find local channels. Everything was LG channels. Otherwise the location, decor and amenities was extraordinary. We will tell our friends about this wonderful place.

Reviewed on Oct 5, 2026

Brewery Park Hotel

Brewery Park Hotel

North End
CA $980
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9/10 Wonderful! (286 reviews)
The Sutton Place Hotel Halifax

The Sutton Place Hotel Halifax

Downtown Halifax
CA $919
per person
Nov 27 - Nov 29
found 19 hours ago
Roundtrip flight included
Ottawa (YOW) to Halifax (YHZ)
9.6/10 Exceptional! (2,292 reviews)
It’s a nice hotel and in a great location. Unfortunately, our room wasn’t cleaned one day. When they did clean it the following day, they didn’t leave behind the standard amenities like lotion. The staff were friendly but initially put us in a room facing another building when there were plenty of nicer rooms available (they moved us, but only when we asked if a better view was available). Small things, but when you pay a lot of money to stay there it’s nice when those small things are proactively addressed

Reviewed on Oct 12, 2026

Red George Inn and Suites

Red George Inn and Suites

Downtown Halifax
CA $878
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
8.8/10 Excellent! (192 reviews)

Things to do near Windsor

Windsor, Nova Scotia, offers a delightful mix of family-friendly activities and outdoor adventures. Enjoy beach vacations, cultural explorations, and brewery tours, or indulge in sensational entertainment. For those who love shopping, the local shopping centre and mall provide a variety of options. Golf enthusiasts will also find excellent courses to play. Whether you're seeking relaxation or adventure, Windsor has something for everyone.

Shopping

In Windsor, you can shop at local boutiques and gift shops for unique souvenirs. If you're up for a drive, Hennigar's Farm Market is 22.5km away, and Tantallon Plaza is 38.6km away, offering a variety of local goods and family-friendly shopping experiences.

Recreation

At Avon Valley Golf and Country Club, enjoy a round of golf surrounded by beautiful landscapes, perfect for sports enthusiasts. Reservoir Park offers a serene retreat for relaxation and wellness, ideal for unwinding in nature. For more golfing, Ken-Wo Golf Club provides stunning outdoor vibes and challenging courses.

Adventure

Experience the thrill of skiing at Ski Martock, located 6.4km from Windsor, where you can enjoy the snowy slopes and vibrant sports atmosphere. For an adrenaline rush, visit Ontree Fun and Adventure Park, also 6.4km away, and conquer their exciting zipline and ropes course amidst nature.

Nightlife

Windsor's nightlife offers a vibrant blend of local pubs and live music. Visit the King's Arms Pub for a cozy atmosphere and great craft beers. For dancing and lively entertainment, check out the popular Windsor Legion, where community spirit thrives and local bands often perform.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Windsor

Windsor, Nova Scotia, offers a delightful mix of family-friendly and outdoor experiences, perfect for a vacation. Explore scenic lakes, fascinating history museums, and historic colleges. For a romantic outing or beach day, consider visiting Windsor Island or attending the Windsor Festival. Don't miss the charming Windsor Castle, adding a touch of history to your trip. Enjoy the diverse attractions that cater to both adventure seekers and culture enthusiasts alike.

  • Haliburton House Museum: Step into the past at Haliburton House Museum, a beautifully preserved historical home showcasing 19th-century life in Nova Scotia. Explore period furnishings and captivating exhibits that highlight the region's cultural heritage.
  • Trecothic Creek and Windsor Railway: Experience the charm of a bygone era at Trecothic Creek and Windsor Railway, where you can ride on vintage trains and learn about the history of rail travel in the area. This interactive museum is a delightful journey for all ages.
  • Grand Pre National Historic Site: Discover the poignant history of the Acadian people at Grand Pre National Historic Site, located 19.3km from Windsor. Wander through beautiful landscapes and visit the memorial church to gain insight into Acadian culture and resilience.

Best time to go to Windsor

The best time to visit Windsor can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Windsor falls in August, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Windsor falls in February, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverageAverage
April40.3°F (4.6°C)Light RainMostly CloudyAverageAverage
May48.4°F (9.1°C)Light RainMostly CloudyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyAverageSlightly High
July64.8°F (18.2°C)Light RainMostly SunnySlightly HighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighAverage
October52.5°F (11.4°C)Light RainMostly SunnyAverageAverage
November43.0°F (6.1°C)Light RainMostly CloudySlightly LowSlightly Low
December34.9°F (1.6°C)Light RainMostly CloudySlightly LowSlightly Low

Tips to save on your trip to Windsor

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Windsor.
  • Consider traveling to Windsor during the low season (November to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ready to book your vacation to Windsor?

Choose your dates

Windsor Hotel Deals

The August House

The August House

494 King St Windsor NS
CA $185
CA $220 total
Nov 4 - Nov 5
includes taxes & fees
10/10 Exceptional! (242 reviews)
"Location for visiting around the area is great. Take time to explore the entire inn before you settle in. Lovely common spaces. You might find a midnight snack surprise for guests in a freezer somewhere."

Reviewed on Oct 12, 2026

The August House
Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS
CA $136
CA $228 total
Oct 27 - Oct 28
includes taxes & fees
9.6/10 Exceptional! (10 reviews)
"Dan reached out with directions on accessing the property ahead of our check in. The process was smooth. Comfortable bed. Nice kitchen to cook in and appliances . We would definitely stay here again. Easy walking access to downtown Windsor"

Reviewed on Oct 11, 2026

Gateway to Annapolis Valley | Windsor Studio Suite
Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS
CA $128
CA $219 total
Oct 19 - Oct 20
includes taxes & fees
Stylish Windsor Suite Near Wineries & Fundy Coast
See all 163 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.
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Stay near popular Windsor attractions

Haliburton House Museum

9.0/10 (2 reviews)
You can spend time studying the exhibits at Haliburton House Museum in Windsor. You can enjoy the wineries while in the area.
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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.
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West Hants Historical Society

7.0/10 (4 reviews)
You can spend time browsing the exhibits at West Hants Historical Society in Windsor. You can enjoy the wineries while in the area.
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Mermaid Theatre of Nova Scotia

7.0/10 (2 reviews)
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.
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Shand House Museum

10.0/10 (1 review)
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.
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Windsor Hockey Heritage Centre

9.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Windsor Hockey Heritage Centre in Windsor. You can enjoy the wineries while in the area.
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Fort Edward National Historic Site

8.8/10 (3 reviews)
You can find out about the history of Windsor when you stop by Fort Edward National Historic Site. You can enjoy the wineries while in the area.
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Dill's Atlantic Giant Pumpkin Farm

Enjoy an outing to Dill's Atlantic Giant Pumpkin Farm during your stay in Windsor. Stroll along the riverfront or experience the area's museums.
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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from CA $441 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.

Explore a world of travel with Expedia

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