Title: Jackson Vacation Packages & Trips 2026 from CA $847 | Expedia.ca

[Hotels in Jackson](https://expedia.ca/Jackson-Hotels.d602318.Travel-Guide-Hotels)[Vacation Rentals in Jackson](https://expedia.ca/Jackson-Vacation-Rentals.d602318.Travel-Guide-VacationRentals)[Flights to Jackson](https://expedia.ca/Cheap-Flights-To-Jackson.d602318.Travel-Guide-Flights)[Jackson Car Rentals](https://expedia.ca/Car-Rentals-In-Jackson.d602318.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)

# Jackson 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 Jackson Vacation

Unforgettable adventures await when you reserve a vacation package to Jackson. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this exciting city. Fill your free time with visits to [Little Switzerland](https://www.expedia.ca/Little-Switzerland-Slinger.d6335509.Vacation-Attraction), [Cabelas](https://www.expedia.ca/Cabelas-Richfield.d553248621532659426.Vacation-Attraction) and [Kettle Moraine Ice Center](https://www.expedia.ca/Kettle-Moraine-Ice-Center-West-Bend.d6335535.Vacation-Attraction), some of the top attractions you shouldn't miss during a trip to Jackson. Expedia is here to help you escape your routine. Tailor your vacation to Jackson to suit your travel style, whatever that may be.

## Top Jackson Vacation Deals

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

![Sheraton Milwaukee Brookfield Hotel](https://images.trvl-media.com/lodging/1000000/10000/9500/9488/ac547b1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sheraton Milwaukee Brookfield Hotel

CA $847

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

8.4/10 Very Good! (500 reviews)

Wonderful stay, clean room, friendly staff, lots of shopping near by

Reviewed on Jan 9, 2026

![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,109

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.8/10 Exceptional! (2,425 reviews)

Great hotel! So fun and unique. Very clean and personalized

Reviewed on Jan 11, 2026

![Kinn Guesthouse Bay View](https://images.trvl-media.com/lodging/21000000/20240000/20233300/20233264/4e3a3faa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Kinn Guesthouse Bay View

Bay View

CA $1,009

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.6/10 Exceptional! (428 reviews)

The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

![The Iron Horse Hotel](https://images.trvl-media.com/lodging/3000000/2100000/2097200/2097106/2030b501_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Iron Horse Hotel

Fifth Ward

CA $1,153

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,008 reviews)

Room ready early. Everything clean and well-kept. Will stay there again.

Reviewed on Jan 7, 2026

![The Brewhouse Inn & Suites](https://images.trvl-media.com/lodging/8000000/7090000/7084400/7084340/c5b60965_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Brewhouse Inn & Suites

Westown

CA $1,008

per person

Mar 29 - Apr 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.4/10 Exceptional! (1,001 reviews)

It would be very helpful clean daily the room

Reviewed on Jan 10, 2026

## Ready to book your vacation to Jackson?

Choose your dates

## Jackson Hotel Deals

![Comfort Inn & Suites Jackson - West Bend](https://images.trvl-media.com/lodging/1000000/670000/661000/660970/aea83804_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Inn & Suites Jackson - West Bend

W227 N16890 Tillie Lake Ct Jackson WI

Fully refundableReserve now, pay when you stay

CA $115

CA $128 total

Jan 29 - Jan 30

includes taxes & fees

8.8/10 Excellent! (570 reviews)

The room was very clean and spacious. It was also very quiet. My teenagers enjoyed the pool and hot tub. Culver’s is right next door. The staff was very friendly. We forgot our thermos in the room and came back for it 4 hours later. Yes, it was waiting for us.

Reviewed on Jan 1, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F01%2F2026&endDate=30%2F01%2F2026&selected=660970&PinnedHotelID=660970&HadPinnedHotel=true&regionId=602318)

![Saint Kate - The Arts Hotel](https://images.trvl-media.com/lodging/1000000/30000/23300/23253/63d91083_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Saint Kate - The Arts Hotel

139 E Kilbourn Ave Milwaukee WI

CA $166

CA $196 total

Jan 15 - Jan 16

includes taxes & fees

9.6/10 Exceptional! (2,520 reviews)

Great staff, amenities and room. Everything was clean and professional

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=15%2F01%2F2026&endDate=16%2F01%2F2026&selected=23253&PinnedHotelID=23253&HadPinnedHotel=true&regionId=602318)

![Ambassador Hotel Milwaukee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/120000/117100/117078/c32357bf_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

2308 W Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $98

CA $116 total

Jan 25 - Jan 26

includes taxes & fees

9/10 Wonderful! (1,268 reviews)

In town for new years

Reviewed on Jan 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=117078&PinnedHotelID=117078&HadPinnedHotel=true&regionId=602318)

[See all 899 properties in Jackson](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&regionId=602318)

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)

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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.

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