Title: Windsor Vacation Packages & Trips 2026 from CA $574 | 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/b4ccdb92-b048-45af-b643-5a9cc297deeb.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Windsor Vacation Packages

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

Photo by Rick Alvarez

- ##  
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.

![Dream catcher](https://images.trvl-media.com/lodging/46000000/45470000/45469900/45469873/6cb35168_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Dream catcher

West Oakland

CA $574

per person

Feb 20 - Feb 23

found 22 hours ago

Roundtrip flight included

Toronto (YTO) to Oakland (OAK)

5.6/10 (87 reviews)

The place is very friendly.!

Reviewed on Mar 30, 2025

![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 $749

per person

Feb 14 - Feb 17

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Oakland (OAK)

8.8/10 Excellent! (1,003 reviews)

Should include free breakfast! It will add more value for the price ( from customer point of view!)

Reviewed on Dec 23, 2025

![DoubleTree by Hilton Hotel Berkeley Marina](https://images.trvl-media.com/lodging/1000000/30000/23800/23800/ba0da8d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DoubleTree by Hilton Hotel Berkeley Marina

Berkeley Marina

CA $1,361

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Oakland (OAK)

8.2/10 Very Good! (3,745 reviews)

Nice spot by the marina. Great staff.

Reviewed on Dec 24, 2025

![Homewood Suites by Hilton Oakland-Waterfront](https://images.trvl-media.com/lodging/1000000/810000/804400/804389/fc341484_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Homewood Suites by Hilton Oakland-Waterfront

San Antonio

CA $1,118

per person

Feb 10 - Feb 15

found 20 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Oakland (OAK)

7.8/10 Good! (664 reviews)

The room was OK at best. Furniture was very dated. Laminate was coming off in the kitchen no central air portable air conditioner that worked OK friendly but I wouldn’t recommend staying there.

Reviewed on Nov 24, 2025

![Holiday Inn Express Hotel & Suites Oakland-Airport by IHG](https://images.trvl-media.com/lodging/1000000/290000/281600/281599/757bfaf5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express Hotel & Suites Oakland-Airport by IHG

Airport District

CA $679

per person

Jan 26 - Jan 30

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Oakland (OAK)

8.8/10 Excellent! (1,001 reviews)

I did not care for breakfast. The sausage was overcooked. The muffins needed more time in the oven. As a baker I look at how baked goods are prepared. The WiFi took too long to access the web.

Reviewed on Dec 19, 2025

## 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 $130

CA $148 total

Jan 4 - Jan 5, 2026

includes taxes & fees

9.2/10 Wonderful! (1,264 reviews)

Clean, helpful staff

Reviewed on Dec 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%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 $130

CA $148 total

Jan 1 - Jan 2, 2026

includes taxes & fees

9/10 Wonderful! (1,026 reviews)

Nice place, helpful staff, clean and quiet, great value

Reviewed on Dec 22, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%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 $138

CA $158 total

Jan 4 - Jan 5, 2026

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

T

Reviewed on Dec 21, 2025

[](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=2292819&PinnedHotelID=2292819&HadPinnedHotel=true&regionId=9542)

[See all 2,112 properties in Windsor](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F12%2F2025&endDate=26%2F12%2F2025&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 wineries. 

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

### What to do in Windsor

![Self Guided Audio Driving Tour from Vancouver to Whistler](https://mediaim.expedia.com/localexpert/49347243/7bf0733f-cee6-4b20-8169-1ef9ede9ca77.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Self-Guided Audio Driving Tour of Sonoma and Napa Valley

CA $23

per traveller

[](https://expedia.ca/things-to-do/self-guided-audio-driving-tour-of-sonoma-and-napa-valley.a49347243.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 $69

per adult

**84%** 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 $196

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

- Lodging
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- [Flights from Fargo (FAR) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/far/sts/fargo-to-santa-rosa)
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- [Flights from Grand Rapids (GRR) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/grr/sts/grand-rapids-to-santa-rosa)
- [Flights from Hagerstown (HGR) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/hgr/sts/hagerstown-to-santa-rosa)
- [Flights from Lake Havasu City (HII) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/hii/sts/lake-havasu-city-to-santa-rosa)
- [Flights from Harlingen (HRL) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/hrl/sts/harlingen-to-santa-rosa)
- [Flights from Jackson Hole (JAC) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/jac/sts/jackson-hole-to-santa-rosa)
- [Flights from Joplin (JLN) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/jln/sts/joplin-to-santa-rosa)
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- [Flights from Los Angeles (LAX) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/lax/sts/los-angeles-to-santa-rosa)
- [Flights from Liberia (LIR) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/lir/sts/liberia-to-santa-rosa)
- [Flights from Lancaster (LNS) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/lns/sts/lancaster-to-santa-rosa)
- [Flights from Morelia (MLM) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/mlm/sts/morelia-to-santa-rosa)
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- [Flights from Seattle Paine Field Intl. Airport (PAE) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/pae/sts/seattle-paine-field-intl-airport-to-santa-rosa)
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- [Flights from Scottsdale (SCF) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/scf/sts/scottsdale-to-santa-rosa)
- [Flights from Seattle (SEA) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/sea/sts/seattle-to-santa-rosa)
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- [Flights from Salt Lake City (SLC) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/slc/sts/salt-lake-city-to-santa-rosa)
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- [Flights from Winnipeg (YWG) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/ywg/sts/winnipeg-to-santa-rosa)
- [Flights from Saskatoon (YXE) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/yxe/sts/saskatoon-to-santa-rosa)
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- [Flights from Toronto (YYZ) to Santa Rosa (STS) ](https://www.expedia.ca/lp/flights/yyz/sts/toronto-to-santa-rosa)

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- [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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