Greendale Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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!
Top Greendale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Pfister Hotel
Downtown Milwaukee
CA $1,064
per person
Dec 4 - Dec 7
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (2,283 reviews)
The Pfister is a such extraordinary place to stay. You can’t go wrong choosing this hotel for your weekend getaway. The staff are wonderful and friendly. They were very accommodating. Check in went smooth with a complimentary glass of champagne. The lobby is such a fun cozy place to enjoy a drink at the bar and sit down by the warm fire. So much history in this hotel. The Pfister is always our first pick choice when staying in Milwaukee. Thank you for the unforgettable stay.
Reviewed on Oct 18, 2026
Ready to book your vacation to Greendale?
Greendale Hotel Deals
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $119
CA $140 total
Nov 9 - Nov 10
includes taxes & fees
8.6/10 Excellent! (1,549 reviews)
"Perfect location to stay when attending the Miller Theater. Great stay all around."
Reviewed on Oct 18, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $90
CA $104 total
Nov 12 - Nov 13
includes taxes & fees
8.4/10 Very good! (1,271 reviews)
"It was our first time staying in the club Room. The buffet breakfast was amazing"
Reviewed on Oct 19, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $168
CA $198 total
Nov 1 - Nov 2
includes taxes & fees
9.6/10 Exceptional! (2,414 reviews)
"Beautiful slave and great location. I don't love that the room requires a keycard to turn the light on but that's a pretty minor inconvenience compared to all the wonderful things that this hotel offers. Walkable area, happy hour reception. Will stay again."
Reviewed on Oct 18, 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
Milwaukee's Riverwalk Walking Tour
CA $22
per adult
100% of travellers recommend
Frequently asked questions
How much does a Greendale vacation package cost?
Offering excellent value package deals from CA $1,024 on Expedia, you'll be surprised at how little a vacation to Greendale costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Greendale?
Plan your trip for the low season and you're likely to get cheap Greendale vacation packages. Keep in mind that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Greendale?
Dedicate at least 6 days for your Greendale vacation to discover everything that makes this destination special. Wander around key neighbourhoods, including Mitchell West and College Heights. Then make a beeline for major sights such as The Rock Sports Complex and Milwaukee Mile. With a well-organized itinerary, you can keep busy with room for some rest time too. Want to venture outside of Greendale? Consider squeezing in an excursion or two.
How to find the best Greendale package deals?
Use Expedia's filters to help you find some of the best 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 want to save, plan your trip for midweek, or browse for Greendale package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Greendale vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and hotels individually. Better still, you can tailor your Greendale trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Greendale?
If you're planning an impromptu Greendale adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Greendale?
- Pick your travel dates: What you plan to do in Greendale and your preferred season can help you decide when to go.
- Set a budget: Consider costs such as flights, food and transportation when calculating how much to save for your trip to Greendale. Then, select a property that suits your budget, whether that's a wallet-friendly option or a deluxe retreat.
- Determine how many days away: Start by making a list of all the attractions and activities you want to get to in Greendale. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Greendale vacation package.
Explore a world of travel with Expedia
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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.
