Greendale Vacations from $608
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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.
The Iron Horse Hotel
Fifth Ward
$909
per person
Nov 23 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,353 reviews)
Beautiful hotel with easily accessible parking garage next door for $26 a day (or valet). The restaurant at the hotel was also great - steak sando was perfect! Very comfortable beds and clean rooms.
Reviewed on Oct 14, 2026
Kinn Guesthouse Bay View
Bay View
$995
per person
Nov 23 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
9.4/10 Exceptional! (505 reviews)
We didn’t get the door code in advance, due to booking through a third party, but they responded quickly to our call. The room was a nice side, but it was loud due to the gap under the door to the hallway. There are also 4 flights of stairs to get to the rooms and no elevators. Be mindful of this if you’re not a light packer. Cleaning staff were present, but never came to freshen our room. The kitchen is shared and well maintained. Great location, however. Walking distance to a bunch of restaurants and bars and a short ride away from even more.
Reviewed on Oct 11, 2026
Stay near popular Greendale attractions
Reiman Publications Visitor Center
After visiting Reiman Publications Visitor Center, make a plan to see the other sights and activities in Greendale. Attend a baseball game or simply enjoy the lively breweries while you're in the area.
What to do in Greendale
Greendale Hotel Deals
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$84 nightly
$99 total
Nov 9 - Nov 10
Total with taxes and fees
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$64 nightly
$73 total
Nov 1 - Nov 2
Total with taxes and fees
8.4/10 Very Good! (1,250 reviews)
"Clean Room."
Reviewed on Oct 14, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$119 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Greendale Vacation Packages
Greendale Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | General Mitchell Intl. Airport (MKE) |
Population | 14,300 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Harley-Davidson Museum, Milwaukee County Zoo and Milwaukee Art Museum |
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Frequently asked questions
How much does a Greendale vacation package cost?
You'll find cheap prices from $608 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
