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

[Hotels in Greendale](https://expedia.ca/Greendale-Hotels.d6335559.Travel-Guide-Hotels)[Vacation Rentals in Greendale](https://expedia.ca/Greendale-Vacation-Rentals.d6335559.Travel-Guide-VacationRentals)[Flights to Greendale](https://expedia.ca/Cheap-Flights-To-Greendale.d6335559.Travel-Guide-Flights)[Greendale Car Rentals](https://expedia.ca/Car-Rentals-In-Greendale.d6335559.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)

# Greendale 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 Greendale Vacation

Say farewell to planning hassles and hello to a Greendale vacation package. With the finer details organized before you go, you can focus on discovering the best of this city, starting with Historic Third Ward, which is great for shopping, festivals and history. Every trip to Greendale needs a well-thought-out itinerary. Fill yours with major attractions such as [American Family Field](https://www.expedia.ca/American-Family-Field-Milwaukee.d6068273.Vacation-Attraction), [Wisconsin State Fair Park](https://www.expedia.ca/Wisconsin-State-Fair-Park-Milwaukee.d6181509.Vacation-Attraction) and [The Rock Sports Complex](https://www.expedia.ca/The-Rock-Sports-Complex-Milwaukee.d637804756223746048.Vacation-Attraction). Stop dreaming and start doing. Explore the multitude of options on Expedia today and put your Greendale vacation plans into motion!

## Top Greendale 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 Greendale?

Choose your dates

## Greendale Hotel Deals

![The Pfister Hotel](https://images.trvl-media.com/lodging/1000000/20000/19500/19467/169f18e6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $197

CA $233 total

Jan 23 - Jan 24

includes taxes & fees

9.4/10 Exceptional! (1,864 reviews)

This is a beautiful historic hotel with a number of wonderful amenities. Unfortunately, we had a few problems with food/drink orders being forgotten both in the Mason Street Grill and room service. The staff handled these situations well by providing free items in compensation. The hotel was also ...

Reviewed on Jan 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=23%2F01%2F2026&endDate=24%2F01%2F2026&selected=19467&PinnedHotelID=19467&HadPinnedHotel=true&regionId=6335559)

![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=6335559)

![Drury Plaza Hotel Milwaukee Downtown](https://images.trvl-media.com/lodging/33000000/32510000/32501800/32501737/ac1d9528_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $139

CA $164 total

Jan 18 - Jan 19

includes taxes & fees

9.6/10 Exceptional! (2,004 reviews)

The hotel was nice. Most of the staff was great. The pool/ hot tub was also really good. My only issue was when I arrived a little after 2pm, I was told my room was not ready and I needed to wait until after 3pm. I saw many other people checking in prior to 3pm and even 2 people checked in prior ...

Reviewed on Jan 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=32501737&PinnedHotelID=32501737&HadPinnedHotel=true&regionId=6335559)

[See all 1,223 properties in Greendale](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&regionId=6335559)

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 Greendale

![Harley-Davidson Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54544-Harley-Davidson-Museum-Milwaukee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Harley-Davidson Museum

5/5(13 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

[](https://expedia.ca/Harley-Davidson-Museum-Menomonee-River-Valley.d6279040.Vacation-Attraction)

![Milwaukee Art Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/219000/219540-Milwaukee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Milwaukee Art Museum

5/5(12 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

[](https://expedia.ca/Milwaukee-Art-Museum-East-Town.d6068277.Vacation-Attraction)

#### Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area. 

[](https://expedia.ca/Potawatomi-Bingo-Casino-Menomonee-River-Valley.d6335076.Vacation-Attraction)

### What to do in Greendale

![2 Hour Milwaukee Scavenger Hunt Game](https://mediaim.expedia.com/localexpert/49296611/4017c436-a1bb-44c8-9945-447fa08e21b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Milwaukee Scavenger Hunt Walking Tour and Game

CA $67

per adult

[](https://expedia.ca/things-to-do/milwaukee-scavenger-hunt-walking-tour-and-game.a49296611.activity-details)

[See all activities in Greendale](https://expedia.ca/things-to-do/search?rid=6335559)

## Explore a world of travel with Expedia

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- [Pettit National Ice Center ](https://www.expedia.ca/Pettit-National-Ice-Center-Milwaukee.d6335062.Vacation-Attraction)
- [Potawatomi Bingo Casino ](https://www.expedia.ca/Potawatomi-Bingo-Casino-Milwaukee.d6335076.Vacation-Attraction)
- [Regency Mall ](https://www.expedia.ca/Regency-Mall-Racine.d6335496.Vacation-Attraction)
- [Reiman Publications Visitor Center ](https://www.expedia.ca/Reiman-Publications-Visitor-Center-Milwaukee.d553248621561863049.Vacation-Attraction)
- [Sanders Park ](https://www.expedia.ca/Sanders-Park-Mount-Pleasant.d553248634993816370.Vacation-Attraction)
- [Silver Lake Vacations ](https://www.expedia.ca/Silver-Lake.d3000462031.Destination-Travel-Guides)
- [Spinning Top and Yo-Yo Museum ](https://www.expedia.ca/Spinning-Top-And-Yo-Yo-Museum-Burlington.d6333597.Vacation-Attraction)
- [Twin Lakes Vacations ](https://www.expedia.ca/Twin-Lakes.d3000462091.Destination-Travel-Guides)
- [Washington County Fair Grounds ](https://www.expedia.ca/Washington-County-Fair-Grounds-West-Bend.d6181503.Vacation-Attraction)
- [Whitefish Bay Vacations ](https://www.expedia.ca/Whitefish-Bay.d6335560.Destination-Travel-Guides)
- [Wind Point Lighthouse ](https://www.expedia.ca/Wind-Point-Lighthouse-Racine.d6094003.Vacation-Attraction)

\* 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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