Greendale Vacation Packages

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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, Wisconsin State Fair Park and The Rock Sports Complex. 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.
Hilton Garden Inn Milwaukee Airport

Hilton Garden Inn Milwaukee Airport

3 out of 5
Price was CA $1,061, price is now CA $912 per person
CA $912
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,001 reviews)
Beds were so comfortable. Rooms spacious and clean. All of the workers were super nice! Definetly would stay again.

Reviewed on Aug. 10, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was CA $1,390, price is now CA $1,148 per person
CA $1,148
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Such a cool place! The room was spacious and clean, and it was a great location for exploring the city. Staff were super friendly, and the food and vibe of the restaurant were great!

Reviewed on Aug. 21, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,360, price is now CA $1,157 per person
CA $1,157
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (1,698 reviews)
Beautiful building and great service

Reviewed on Aug. 16, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,264, price is now CA $1,082 per person
CA $1,082
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (402 reviews)
The beds are so comfortable and the decor is great! There is really no staff there to connect with, which is different. You go and leave like its an apartment- they just send codes and there is no service desk. I loved the place! Very steep stairs for older people to go up.

Reviewed on Aug. 10, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,290, price is now CA $1,109 per person
CA $1,109
per person
Nov 7 - Nov 11
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.8/10 Exceptional! (2,385 reviews)
Manager checked in on us personally! Beds were comfortable! Wished there was coffee in rooms instead of hallway.

Reviewed on Aug. 15, 2025

Ready to book your vacation to Greendale?

 

Choose your dates

Greendale Hotel Deals

Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Aug 28 to Aug 29
CA $121
CA $139 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (1,255 reviews)
"Very nice weekend stay"

Reviewed on Aug. 18, 2025

Sonesta Select Milwaukee Brookfield
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 1 to Sep 2
CA $204
CA $241 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,340 reviews)
"The staff was super friendly. The place was clean. Security was great. I would stay here again, no questions asked."

Reviewed on Aug. 18, 2025

Potawatomi Hotel & Casino
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Aug 27 to Aug 28
CA $177
CA $209 total
Aug 27 - Aug 28
includes taxes & fees
9.6/10 Exceptional! (1,842 reviews)
"Very nice property, easy parking!"

Reviewed on Aug. 19, 2025

Drury Plaza Hotel Milwaukee Downtown
See all 1,334 properties in Greendale
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Greendale

Harley-Davidson Museum featuring interior views

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.

Harley-Davidson Museum
Milwaukee Art Museum

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.

Milwaukee Art Museum

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.

Potawatomi Bingo Casino

What to do in Greendale

Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
A Romantic Journey Through Milwaukee

A Romantic Journey Through Milwaukee

CA $1,077
per adult
A Romantic Journey Through Milwaukee
At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

CA $36
per adult
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
See all activities in Greendale

Frequently asked questions

How much does a Greendale vacation package cost?
Offering excellent value package deals from CA $912 on Expedia, you'll be surprised at how little a vacation to Greendale costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Greendale?
Plan your trip for the low season and you're likely to get cheap Greendale vacation packages. Keep in mind that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Greendale?
Dedicate at least 6 days for your Greendale vacation to discover everything that makes this destination special. Wander around key neighbourhoods, including Mitchell West and College Heights. Then make a beeline for major sights such as The Rock Sports Complex and Milwaukee Mile. With a well-organized itinerary, you can keep busy with room for some rest time too. Want to venture outside of Greendale? Consider squeezing in an excursion or two.
How to find the best Greendale package deals?
Use Expedia's filters to help you find some of the best Greendale package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Greendale package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Greendale vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can tailor your Greendale trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Greendale?
If you're planning an impromptu Greendale adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Greendale?

  1. Pick your travel dates: What you plan to do in Greendale and your preferred season can help you decide when to go.
  2. Set a budget: Consider costs such as flights, food and transportation when calculating how much to save for your trip to Greendale. Then, select a property that suits your budget, whether that's a wallet-friendly option or a deluxe retreat.
  3. Determine how many days away: Start by making a list of all the attractions and activities you want to get to in Greendale. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Greendale vacation package.

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