Windsor Vacations from $1,006

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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.
Hampton Inn by Hilton Halifax Downtown

Hampton Inn by Hilton Halifax Downtown

Downtown Halifax
$1,006
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.6/10 Excellent! (1,266 reviews)
CLIPPER SHIPP BEACH MOTEL

CLIPPER SHIPP BEACH MOTEL

$1,162
per person
Sep 20 - Sep 27
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Halifax (YHZ)
9.2/10 Wonderful! (192 reviews)
Sandman Signature Dartmouth Hotel & Suites

Sandman Signature Dartmouth Hotel & Suites

$1,222
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Halifax (YHZ)
9.4/10 Exceptional! (2,713 reviews)
Coastal Inn Halifax

Coastal Inn Halifax

$1,040
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Halifax (YHZ)
8.6/10 Excellent! (1,017 reviews)
Residence Inn by Marriott Halifax Downtown

Residence Inn by Marriott Halifax Downtown

Downtown Halifax
Save 100% on your flight
$2,005
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Halifax (YHZ)
8.6/10 Excellent! (1,000 reviews)
For the high cost of our basic room, I would have expected more. The 4th floor smelled of old gravy all weekend long, the elevator smelled of hot garbage. Our room was fine upon first glance. Then I noticed toothpaste that had not been cleaned off the bathroom wall, mirror had something sprayed on it, and our shower was missing one of its glass sliding doors. It was a busy weekend so we just dealt with it all rather than requesting another room after we had already settled in. However, I would suggest booking elsewhere at this price. 4 star prices with a 2 star experience.

Reviewed on Aug 11, 2026

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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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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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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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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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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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Fountain Cultural & Performing Arts Centre

Enjoy an outing to Fountain Cultural & Performing Arts Centre during your stay in Windsor. Take in the museums and countryside 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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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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Windsor Hotel Deals

The August House

The August House

494 King St Windsor NS
$133 nightly
$156 total
Sep 1 - Sep 2
Total with taxes and fees
10/10 Exceptional! (201 reviews)
"Everything was beautiful. They set out a variety of amenities for their guests to have for free, which includes granola little bags of chips, little pieces of chocolate, coffee, tea, water there’s a little fridge in our room that we could keep things in the bathroom was beautiful and clean."

Reviewed on Aug 8, 2026

The August House
Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite

Windsor NS
$133 nightly
$152 total
Aug 19 - Aug 20
Total with taxes and fees
9.4/10 Exceptional! (3 reviews)
"Very clean, comfortable space. We enjoyed our stay."

Reviewed on Jul 28, 2026

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

Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor NS
$163 nightly
$186 total
Aug 19 - Aug 20
Total with taxes and fees
10/10 Exceptional! (1 review)
"The accommodation was impeccably clean and well appointed with everything a traveller would require. Lots of coffee, close distance to amenities, shops, restaurants and more. I would certainly return and hopefully, stay longer !"

Reviewed on Aug 10, 2026

Stylish Windsor Suite Near Wineries & Fundy Coast
See all 159 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.

Find the Best Windsor Vacation Packages

Things to do in and around Windsor

Windsor, Nova Scotia, offers a delightful mix of family-friendly activities and outdoor adventures. Visitors can enjoy shopping at local centers and malls, while also exploring leisurely excursions and day outings. Whether you're interested in skiing in the winter or discovering the beautiful landscapes, Windsor provides a perfect backdrop for a memorable vacation experience.

Shopping

For a delightful shopping experience in Windsor, visit Hennigar's Farm Market, which offers local produce and unique gifts just 14 miles away. If you're up for a drive, Hubbards Farmer's Market and Tantallon Plaza, both 25 and 24 miles away respectively, offer family-friendly vibes and a variety of local goods.

Recreation

At the Mermaid Theatre of Nova Scotia, enjoy captivating performances in a charming setting that fosters culture and family connection. For relaxation, head to Reservoir Park, where serene nature invites wellness and tranquility. For outdoor enthusiasts, Ken-Wo Golf Club offers a refreshing golfing experience amidst beautiful landscapes.

Adventure

At Ski Martock, located 4 miles from Windsor, experience thrilling skiing and snowboarding with scenic views. Ontree Fun and Adventure Park, also 4 miles away, offers exhilarating ziplining and ropes courses for outdoor enthusiasts. For family fun, visit Atlantic Playland, 26 miles from Windsor, featuring exciting water attractions.

Nightlife

Windsor's nightlife offers a cozy charm with local pubs like the King's Arms, where you can enjoy live music and craft beers. For a more upscale experience, visit the Waterfront Grill, perfect for a relaxing dinner with stunning views of the Avon River.

*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 outdoor adventures and rich history, making it perfect for family and romantic getaways. Explore scenic lakes, visit engaging museums, and stroll through historic college campuses. Don’t miss the beautiful Windsor Riverfront for a relaxing day by the water. With so much to see and do, Windsor caters to all types of travelers seeking unique experiences.

  • Haliburton House Museum: Step back in time at Haliburton House Museum, where you can explore the rich history of the area. This charming museum showcases period furnishings and exhibits that reflect the life of one of Nova Scotia's prominent figures, offering visitors a glimpse into the past.
  • Shand House Museum: Discover the Shand House Museum, a delightful venue that highlights local heritage. With its unique architecture and cultural exhibits, this museum provides insight into Windsor's history and the stories of its residents, making it a captivating stop for history buffs.
  • Fundy Centennial Park: Enjoy the great outdoors at Fundy Centennial Park, a family-friendly urban park located 6 miles from Windsor. With scenic walking trails, picnic areas, and stunning views of the Bay of Fundy, it’s the perfect spot for a day of relaxation and exploration.

Best time to go to Windsor

The best time to visit Windsor is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. February is its coolest month on average. At this time, 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 during the off-peak season (typically November to January) for more affordable package holidays to Windsor.
  • 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.

Windsor Essential Information

Language
English
Currency
Canadian dollars
Population
3,900
Max Temp Winter
35ºF
Max Temp Summer
70ºF
Top Sights
Ski Martock, Smileys Provincial Park and West Hants Historical Society

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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 $1,006 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.

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