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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
8.4/10 Very Good! (1,000 reviews)
Older property, friendly staff

Reviewed on Jul. 14, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
9.4/10 Exceptional! (1,009 reviews)
The valet was sketchy. The guy was asking really personal questions. When we left, my wife couldn't find her laptop. She had left it in the car. Thankfully the manager had located it when she called. It was in the lost abd found, turned in by the valet. We can't prove anything but it was really bizarre. We had the same valet again when we left, before we realized the laptop was gone. He did not say anything to us about finding the laptop and turning it in. We were the only car at the entrance when we pulled in so he would have known it was us in the case that it was "lost". Never staying there again.

Reviewed on Jul. 31, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
9.4/10 Exceptional! (1,006 reviews)
We came here for a Bucks game and loved being able just to walk to the game. There were plenty of restaurants within walking distance as well. The common areas were unique and comfortable for playing board games, and the room decor was something special as well.

Reviewed on Aug. 2, 2025

Aloft Milwaukee Downtown

Aloft Milwaukee Downtown

3 out of 5
Westown
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
8.4/10 Very Good! (1,010 reviews)
Very nice hotel, within close walking distance of Fiserv and many restaurants

Reviewed on Jul. 30, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Milwaukee (MKE)
9.8/10 Exceptional! (2,368 reviews)
Saint Kate is a beautiful, funky hotel with one of the best beds I've ever slept on.

Reviewed on Aug. 2, 2025

Ready to book your vacation to Greendale?

 

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Greendale Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Aug 28 to Aug 29
CA $255
CA $301 total
Aug 28 - Aug 29
includes taxes & fees
9.4/10 Exceptional! (1,681 reviews)
"A great experience!"

Reviewed on Jul. 31, 2025

The Pfister Hotel
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Aug 10 to Aug 11
CA $120
CA $139 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (357 reviews)
"Enjoy my stay"

Reviewed on Jul. 30, 2025

Sheraton Milwaukee Brookfield Hotel
AmericInn by Wyndham Glendale/Milwaukee

AmericInn by Wyndham Glendale/Milwaukee

2.5 out of 5
5110 N Port Washington Rd, (772), Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $88 per night from Aug 3 to Aug 4
CA $88
CA $102 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,010 reviews)
"The property is steps away from a great walking trail and park, which hosts a wonderful market on Sundays. Other stores, including Trader Joe's, is a 4 minute walk from the property also. The staff was generally helpful but were sometimes a little too attached to their cell phones. The room was clean ..."

Reviewed on Aug. 2, 2025

AmericInn by Wyndham Glendale/Milwaukee
See all 1,386 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

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

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
Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $114
per adult
Small Group Kayak Tour of Skyline in Milwaukee
Kayaks Rentals Everyday

Milwaukee Kayak Rental

CA $75
per adult
Milwaukee Kayak Rental
See all activities in Greendale

Frequently asked questions

How much does a Greendale vacation package cost?
Offering excellent value package deals from CA $1,107 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.