Greendale Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Greendale
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
S$117
24 Aug - 25 Aug
includes taxes & fees
8/10 Very good! (1,526 reviews)
"Room was better than expected, property well maintained. Breakfast was ok -- regular coffee was not working, yet had 2 personal coffee in the room - which was fine. Pool was good, although smaller than we hoped -- I call it a bonus either way. I'd go back to the place."
Reviewed on 23 Aug, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
S$219
13 Sept - 14 Sept
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
S$119
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (1,130 reviews)
"Thermostat in our room did not work so air conditioning stayed on whole time and room did not get above 65 degrees. Remote batteries didn’t work took a bit for someone to come give us new oned"
Reviewed on 22 Aug, 2026
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.
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
Skip the Line: Museum Admission Ticket - Grohmann Museum
S$6
per adult
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
S$12
per adult
80% of travellers recommend
Frequently asked questions
How much does a Greendale holiday package cost?
You'll find cheap prices on Expedia for your Greendale break. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Greendale costs.
What are the cheapest months to go to Greendale?
To pick up cheap Greendale holiday packages, plan your getaway outside of peak times like public holidays and major festivals. You'll typically find lower prices and better availability when it's less busy.
How many days is enough for Greendale?
The ideal length for your Greendale holiday depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to check out all the main attractions and explore some hidden gems 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 holiday package well in advance.
Is it cheaper to book a Greendale holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and accommodation individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Greendale?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Greendale.
- Plan your budget wisely: As well as the cost of your accommodation, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could arise during your trip to Greendale.
- Decide your trip length: Consider how long you want to spend discovering Greendale. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Greendale holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
