Greendale Vacations from $285

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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!

The Latest Greendale vacation packages

Price found within the past 48 hours. Click for updated prices.
Grandstay Residential Suites Hotel - Sheboygan
The Pfister Hotel
Washington House Inn
Saint Kate - The Arts Hotel
Super 8 by Wyndham Sturtevant/Racine
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Discover the most popular places to visit in Greendale

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Greendale Hotel Deals

Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 1 to Sep 2
$107 total
Sep 1 - Sep 2
Total with taxes and fees
7.4/10 Good! (1,586 reviews)
Clean and secure
"Property is secure and fairly clean. I would stay here again. They are nearing a renovation time so the restaurant wasnt open. Coffee in room is K cup style so you can bring your own but the 2 pods provided were good. Shower had decent pressure. Would like to see more chains offering bidets, but ..."

Reviewed on Aug 21, 2025

Sonesta Milwaukee West Wauwatosa
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
$87 nightly
The price is $100 total per night from Aug 31 to Sep 1
$100 total
Aug 31 - Sep 1
Total with taxes and fees
8/10 Very Good! (1,258 reviews)
"place needs more cleaning specially their amenities"

Reviewed on Aug 20, 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
$155 nightly
The price is $183 total per night from Sep 1 to Sep 2
$183 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,347 reviews)
"People visting the property were not friendly."

Reviewed on Aug 20, 2025

Potawatomi Hotel & Casino
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.

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Frequently asked questions

How much does a Greendale vacation package cost?
You'll find cheap prices from $285 on Expedia for your Greendale break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Greendale costs.
What are the cheapest months to go to Greendale?
January, October and December are great times to search for cheap Greendale vacation packages. Opting to travel in quieter periods means you can typically find better prices on accommodations and flights.
How many days is enough for Greendale?
The ideal length of your Greendale vacation depends on what you'd like to see. Typically, a few days to a week will give you time to hit all the top attractions and explore some hidden spots along the way.
How to find the best Greendale package deals?
Use Expedia's filter tool to help you find some fabulous 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're looking to save, plan your trip for midweek, or look for Greendale package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Greendale vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations individually. Better still, you can customize your Greendale trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Greendale?
Secure amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Greendale break.
Does Expedia offer Book Now, Pay Later Greendale vacation packages?
Your Greendale getaway is meant to be an escape from your busy life, not a reason for money worries. So to give you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.