Greendale Vacations from $663

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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.
Cambria Hotel Milwaukee Downtown

Cambria Hotel Milwaukee Downtown

3 out of 5
Westown
Price was $698, price is now $663 per person
$663
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
8.2/10 Very Good! (1,000 reviews)
My stay was great. Clean room and pleasant staff.

Reviewed on Jan 24, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $848, price is now $771 per person
$771
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Room was great, the house staff were friendly and it genuinely felt welcoming.

Reviewed on Jan 26, 2026

County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Downtown Milwaukee
Price was $786, price is now $716 per person
$716
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.6/10 Exceptional! (1,003 reviews)
Friendly and efficient.

Reviewed on Jan 25, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $756, price is now $739 per person
$739
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.4/10 Exceptional! (316 reviews)
The room was great and the staff was very polite. Guadalupe from the entertainment department, is doing a great job keeping everyone entertained.

Reviewed on Jan 1, 2026

Kasa Westown Milwaukee

Kasa Westown Milwaukee

4 out of 5
Westown
Price was $716, price is now $701 per person
$701
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9/10 Wonderful! (116 reviews)
Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions.

Reviewed on Dec 6, 2025

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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
$150 nightly
The price is $177 total per night from Feb 22 to Feb 23
$177 total
Feb 22 - Feb 23
Total with taxes and fees
9.4/10 Exceptional! (1,920 reviews)
With extra frigid cold weather, we didn’t need to leave the hotel. Enough to keep us busy, relax in the lobby by the fireplace and play cards, great restaurants, a spa and a gym… they had it all. We ate at Mason Street Grill and the Lobby lounge as well as the cafe for breakfast. All the food was ...

Reviewed on Jan 26, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $142 total per night from Feb 9 to Feb 10
$142 total
Feb 9 - Feb 10
Total with taxes and fees
9.6/10 Exceptional! (2,537 reviews)
Fun hotel, great staff. We had a room mixup and although they were unable to switch us to our reserved accommodations, they were very apologetic and offered us a generous credit and also agreed to free parking when asked.

Reviewed on Jan 26, 2026

Saint Kate - The Arts Hotel
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
$100 nightly
The price is $118 total per night from Feb 8 to Feb 9
$118 total
Feb 8 - Feb 9
Total with taxes and fees
9.6/10 Exceptional! (2,026 reviews)
The room was great, the staff was great, the parking was convenient, the location was great, the breakfast and afternoon meals were great!

Reviewed on Jan 24, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,225 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.

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 $663 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.