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*
- 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
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.
Home2 Suites by Hilton Milwaukee Downtown
Downtown Milwaukee
CA $956
per person
Jan 3 - Jan 5
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.8/10 Excellent! (1,009 reviews)
Great location. Walkable to many attractions and the lakefront. Great pricing and wonderful establishment. Clean, friendly professional staff, great breakfast.
Reviewed on Oct 11, 2026
Kinn Guesthouse Downtown
Downtown Milwaukee
CA $1,093
per person
Jan 3 - Jan 5
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (432 reviews)
Interesting concept, wasn't sure at first but really liked it in the end, it's done through codes, etc. No one really at a front desk, but it's OK.
The room was great, very comfortable bed and a great shower.
Location is excellent, close to the public market and other fun things.
Parking is off site, about a half block away, very easy but if it's terrible weather, plan accordingly.
The common kitchen is great. Coffee and tea available, your own spot in the fridge, etc. When we were there, a family was having their after wedding breakfast in the space and it accommodated about 20 just fine.
Would absolutely stay again and recommend.
Reviewed on Oct 10, 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 $133
CA $156 total
Nov 1 - Nov 2
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $91
CA $105 total
Nov 1 - Nov 2
includes taxes & fees
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $170
CA $200 total
Nov 1 - Nov 2
includes taxes & fees
9.6/10 Exceptional! (2,416 reviews)
"The room was clean and good size. The breakfast was great. The 5:30 kickback is the best. Great location as well. Would recommend definitely."
Reviewed on Oct 11, 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 $956 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.
