Title: Windsor Vacation Packages & Trips 2026 from CA $240 | Expedia.ca

[Windsor Travel Guide](https://expedia.ca/Windsor.dx181861)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d181861.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d181861.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.ca/Cheap-Flights-To-Windsor.d181861.Travel-Guide-Flights)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d181861.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windsor Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
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](https://www.expedia.ca/Ski-Martock-Windsor-Forks.d6089495.Vacation-Attraction), [Avon River Heritage Society Museum](https://www.expedia.ca/Avon-River-Heritage-Society-Museum-Avondale.d6309448.Vacation-Attraction) and [Mermaid Theatre of Nova Scotia](https://www.expedia.ca/Mermaid-Theatre-Of-Nova-Scotia-Windsor.d6089633.Vacation-Attraction). 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.

![Hearthstone Inn Boutique Hotel Halifax - Dartmouth](https://images.trvl-media.com/lodging/1000000/20000/12000/11975/2ecf241c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hearthstone Inn Boutique Hotel Halifax - Dartmouth

CA $240

per person

Feb 14 - Feb 16

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Halifax (YHZ)

7.4/10 Good! (1,004 reviews)

The staff was so helpful and friendly

Reviewed on Dec 13, 2025

![Inn on the Lake](https://images.trvl-media.com/lodging/1000000/60000/53000/52922/ac3a7a08_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Inn on the Lake

CA $308

per person

Feb 14 - Feb 16

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Halifax (YHZ)

8.8/10 Excellent! (1,002 reviews)

The room was ok. It seemed old and dated and we are not fans of carpeting.

Reviewed on Dec 14, 2025

![Glengarry Extended Stays](https://images.trvl-media.com/lodging/81000000/80970000/80962400/80962380/4ef25c20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Glengarry Extended Stays

CA $900

per person

Feb 7 - Feb 14

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

8.4/10 Very Good! (661 reviews)

Great room, loved the restaurant, easy access to the Community Centre.

Reviewed on Dec 14, 2025

![Digby Pines Golf Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/890100/890065/5913a6d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Digby Pines Golf Resort and Spa

CA $801

per person

Feb 7 - Feb 14

found 1 hour ago

Roundtrip flight included

Toronto (YYZ) to Halifax (YHZ)

8/10 Very Good! (1,040 reviews)

Rooms are quite dated and not very well laid out. TV is in an awkward place. Plumbing didn’t work quite right. Finishing are very date. Beds are very comfortable and the. Breakfast was awesome. Chose this spot as I got a deal through Expedia with my points but likely wouldn’t choose it as an option at full price.

Reviewed on Dec 7, 2025

![HFX Airport Hotel](https://images.trvl-media.com/lodging/1000000/530000/528300/528264/8c5013ba_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### HFX Airport Hotel

CA $320

per person

Feb 14 - Feb 16

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Halifax (YHZ)

8.2/10 Very Good! (2,821 reviews)

Room was clean and staff fine. Breakfast offerings were bleak, Felt yogurt could have been included,

Reviewed on Dec 14, 2025

## Ready to book your vacation to Windsor?

Choose your dates

## Windsor Hotel Deals

![The August House](https://images.trvl-media.com/lodging/93000000/92030000/92024900/92024852/20fd8b43_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The August House

494 King St Windsor NS

CA $187

CA $223 total

Dec 30 - Dec 31

includes taxes & fees

9.8/10 Exceptional! (148 reviews)

Breakfast menu was made with locally sourced products, tons of gluten free options made in house. The room was amazing. Our stay was amazing and the staff were so kind and attentive

Reviewed on Dec 8, 2025

[](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=92024852&PinnedHotelID=92024852&HadPinnedHotel=true&regionId=181861)

### 

Meander In Bed and Breakfast

153 Albert St Windsor NS

[Get rates](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=35863428&PinnedHotelID=35863428&HadPinnedHotel=true&regionId=181861)

[](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=35863428&PinnedHotelID=35863428&HadPinnedHotel=true&regionId=181861)

![Old Orchard Inn](https://images.trvl-media.com/lodging/1000000/910000/903300/903228/b38dda0d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Old Orchard Inn

153 Greenwich Rd. South Wolfville Ridge NS

Fully refundableReserve now, pay when you stay

CA $219

CA $261 total

Dec 16 - Dec 17

includes taxes & fees

8.4/10 Very Good! (1,004 reviews)

.

Reviewed on Dec 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=903228&PinnedHotelID=903228&HadPinnedHotel=true&regionId=181861)

[See all 117 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&regionId=181861)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### 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. 

[](https://expedia.ca/Haliburton-House-Museum-Windsor.d6301701.Vacation-Attraction)

#### 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. 

[](https://expedia.ca/Trecothic-Creek-And-Windsor-Railway-Windsor.d6309456.Vacation-Attraction)

## Explore a world of travel with Expedia

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- [Falmouth Vacation Rentals ](https://www.expedia.ca/Falmouth-Vacation-Rentals.d6310356.Travel-Guide-VacationRentals)

- [Things to do in Falmouth ](https://www.expedia.ca/Things-To-Do-In-Falmouth.d6310356.Travel-Guide-Activities)

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

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