Greendale Vacations from $407

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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, 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.
Holiday Inn Express Hotel & Suites Milwaukee Airport by IHG
The Iron Horse Hotel
Hampton Inn & Suites Milwaukee Downtown
Potawatomi Hotel & Casino
Saint Kate - The Arts Hotel
Don't see what you're looking for?
See all available trips from Columbus to Greendale
View all trips

Discover the most popular places to visit in Greendale

What to do in Greendale

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
$205 nightly
The price is $242 total per night from Aug 28 to Aug 29
$242 total
Aug 28 - Aug 29
Total includes taxes and 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
$87 nightly
The price is $100 total per night from Aug 10 to Aug 11
$100 total
Aug 10 - Aug 11
Total includes taxes and fees
8.4/10 Very Good! (354 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
$63 nightly
The price is $73 total per night from Aug 11 to Aug 12
$73 total
Aug 11 - Aug 12
Total includes taxes and 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
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.

More vacations you might like

Frequently asked questions

How much does a Greendale vacation package cost?
You'll find cheap prices from $407 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.