Title: Windsor Vacation Packages & Trips 2026 from CA $1,241 | Expedia.ca

[Windsor Travel Guide](https://expedia.ca/Windsor.dx9542)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d9542.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d9542.Travel-Guide-VacationRentals)[Things to do in Windsor](https://expedia.ca/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide)

![](https://images.trvl-media.com/place/9542/d9e00ba9-f670-4899-b5c8-328b2d3d7939.jpg?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

Uncover the best parts of Windsor with a customized Windsor vacation package. From its lively atmosphere and cultural experiences to its spectacular views, you'll love experiencing this picturesque city the way you want to. Like to start exploring your surroundings? [Windsor Golf Club](https://www.expedia.ca/Windsor-Golf-Club-Windsor.d6327439.Vacation-Attraction), [Sonoma-Cutrer Vineyards Cutrer Vineyard](https://www.expedia.ca/Sonoma-Cutrer-Vineyards-Cutrer-Vineyard-Windsor.d553248621532640647.Vacation-Attraction) and [Windsor Oaks Vineyards](https://www.expedia.ca/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction) are three of the top places to visit during a trip to Windsor. Browse Expedia's wide range of travel options and start planning your ideal vacation to Windsor now.

## Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Claremont Resort & Club](https://images.trvl-media.com/lodging/1000000/10000/6700/6609/d997dca7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Claremont Resort & Club

Claremont Hills

CA $1,241

per person

May 6 - May 10

found 6 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

8.8/10 Excellent! (1,003 reviews)

Clean, comfortable, amazing amenities

Reviewed on Feb 24, 2026

![RiverPointe Napa Valley Resort](https://images.trvl-media.com/lodging/2000000/1410000/1400600/1400504/0519f20f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### RiverPointe Napa Valley Resort

Stonehouse

CA $1,383

per person

May 6 - May 13

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

8.8/10 Excellent! (1,344 reviews)

Quiet, walking trail along the river

Reviewed on Feb 23, 2026

![The Meritage Resort and Spa](https://images.trvl-media.com/lodging/2000000/1380000/1372900/1372889/135724b2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Meritage Resort and Spa

Soscol Gateway South

CA $2,397

per person

May 6 - May 13

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

8.2/10 Very Good! (1,003 reviews)

The service was excellent

Reviewed on Feb 24, 2026

![Vino Bello Resort](https://images.trvl-media.com/lodging/2000000/1510000/1509800/1509748/c9623434_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Vino Bello Resort

Soscol Gateway South

CA $1,954

per person

May 6 - May 13

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

8.4/10 Very Good! (1,001 reviews)

Very clean and spacious

Reviewed on Jan 24, 2026

![Bel Abri Napa Valley Inn](https://images.trvl-media.com/lodging/1000000/920000/911000/910902/2b5d1dab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bel Abri Napa Valley Inn

Central Napa

CA $1,412

per person

May 6 - May 13

found 4 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

9.6/10 Exceptional! (1,005 reviews)

Comfortable space with a very good breakfast. Complimentary wine was a nice touch.

Reviewed on Feb 20, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_9542)

## Ready to book your vacation to Windsor?

Choose your dates

## Windsor Hotel Deals

![Holiday Inn Express® Windsor Sonoma Wine Country by IHG](https://images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/6e9c3a9c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Express® Windsor Sonoma Wine Country by IHG

8865 Conde Lane Windsor CA

Fully refundable

CA $141

CA $161 total

Mar 1 - Mar 2

includes taxes & fees

9.2/10 Wonderful! (1,311 reviews)

Great room & breakfast.

Reviewed on Feb 16, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=1273394&PinnedHotelID=1273394&HadPinnedHotel=true&regionId=9542)

![Holiday Inn Windsor Wine Country by IHG](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/48ef5836_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Windsor Wine Country by IHG

8755 Old Redwood Hwy Windsor CA

Fully refundable

CA $135

CA $154 total

Mar 1 - Mar 2

includes taxes & fees

9/10 Wonderful! (1,039 reviews)

The staff was very nice. The room was fine. But it’s very “okay”—I don’t quite understand why it has such high ratings. My biggest disappointment was that the indoor pool that they publicized as year-round is not heated in the winter, so was way too cold for comfortable swimming in February.

Reviewed on Feb 19, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=13235845&PinnedHotelID=13235845&HadPinnedHotel=true&regionId=9542)

![Hampton Inn & Suites Windsor - Sonoma Wine Country](https://images.trvl-media.com/lodging/3000000/2300000/2292900/2292819/d8f70637_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn & Suites Windsor - Sonoma Wine Country

8937 Brooks Road South Windsor CA

Fully refundableReserve now, pay when you stay

CA $167

CA $191 total

Mar 8 - Mar 9

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

Clean room. Good customer service. Amenities needed refilling (soap, conditioner and body wash). Nice breakfast. Needed hotter coffee and salsa with the eggs. Hot tub was a warm tub.

Reviewed on Feb 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=2292819&PinnedHotelID=2292819&HadPinnedHotel=true&regionId=9542)

[See all 2,118 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&regionId=9542)

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

#### Windsor Oaks Vineyards

You can enjoy a tasting or tour at Windsor Oaks Vineyards during your travels to Windsor. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants. 

[](https://expedia.ca/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction)

### What to do in Windsor

![Shopping in Healdsburg](https://mediaim.expedia.com/localexpert/44619999/cbefff56-05ae-409f-96d9-7d58ce9a1052.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### History Walking Tour of Healdsburg

CA $61

per adult

[](https://expedia.ca/things-to-do/history-walking-tour-of-healdsburg.a44619999.activity-details)

![Fine wines paired with tapas-sized portions of food](https://mediaim.expedia.com/localexpert/674597/a5e5b634-bbd9-45cf-abb9-ecde2c3f9a0d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Icon Wine & Food Pairing at Williamson Wines in Healdsburg

CA $68

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/icon-wine-food-pairing-at-williamson-wines-in-healdsburg.a674597.activity-details)

![Healdsburg Wine and Food Pairing Walking Tour](https://mediaim.expedia.com/localexpert/2160900/a9a08d53-fff5-4e22-b145-5995c474ae04.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Healdsburg Wine and Food Pairing Guided Walking Tour

CA $190

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/healdsburg-wine-and-food-pairing-guided-walking-tour.a2160900.activity-details)

[See all activities in Windsor](https://expedia.ca/things-to-do/search?rid=9542)

## Explore a world of travel with Expedia

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- [Middletown Vacations ](https://www.expedia.ca/Middletown.d180934.Destination-Travel-Guides)
- [Occidental Vacations ](https://www.expedia.ca/Occidental.d500727.Destination-Travel-Guides)
- [Old Faithful Geyser of California ](https://www.expedia.ca/Old-Faithful-Geyser-Of-California-Calistoga.d6065829.Vacation-Attraction)
- [Osmosis Day Spa Sanctuary ](https://www.expedia.ca/Osmosis-Day-Spa-Sanctuary-Sebastopol.d553248621532640642.Vacation-Attraction)
- [River Rock Casino ](https://www.expedia.ca/River-Rock-Casino-Geyserville.d6327089.Vacation-Attraction)
- [Robert Louis Stevenson Museum ](https://www.expedia.ca/Robert-Louis-Stevenson-Museum-St-Helena.d6065831.Vacation-Attraction)
- [Santa Rosa Vacations ](https://www.expedia.ca/Santa-Rosa.d3288.Destination-Travel-Guides)
- [Sharpsteen Museum ](https://www.expedia.ca/Sharpsteen-Museum-Calistoga.d6065819.Vacation-Attraction)
- [Soda Rock Winery ](https://www.expedia.ca/Soda-Rock-Winery-Healdsburg.d6324674.Vacation-Attraction)
- [Sonoma Coast State Park ](https://www.expedia.ca/Sonoma-Coast-State-Park-California.d6326892.Vacation-Attraction)
- [Sonoma County Vacations ](https://www.expedia.ca/Sonoma-County.d553248621593965866.Destination-Travel-Guides)
- [Spring Lake Park ](https://www.expedia.ca/Spring-Lake-Park-Santa-Rosa.d6327420.Vacation-Attraction)
- [Villa Grande Vacations ](https://www.expedia.ca/Villa-Grande.d3000428920.Destination-Travel-Guides)
- [Windsor Oaks Vineyards ](https://www.expedia.ca/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction)

- [Rental cars Sonoma County airport ](https://www.expedia.ca/Car-Rentals-In-Sonoma-County.d6032115.Car-Rental-Guide)
- [Enterprise Rental Cars in Sonoma County ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Sonoma-County.d6032115-c15.Car-Rental-Guide-Suppliers)

\* 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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