Greendale Vacation Packages

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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 Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,293, price is now CA $1,040 per person
CA $1,040
per person
Sep 11 - Sep 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,192 reviews)
Seriously one of my all time favorite stays! If Im ever back in Milwaukee, this would be my choice. I even happened to be there on Biker night. Live performance and people on bikes. The hotel is so gorgeously designed and the room was huge, clean and modern. This is on the favs list.

Reviewed on Jul 10, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,231, price is now CA $1,341 per person
CA $1,341
per person
Sep 11 - Sep 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Historic

Reviewed on Jul 11, 2026

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
Price was CA $2,288, price is now CA $1,784 per person
CA $1,784
per person
Aug 20 - Aug 25
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,007 reviews)
Everything seemed clean and well kept. The resort is cute and everything you would expect from a lake resort. Overall the property is dated and the pools are too small for the crowd size around the 4th of July weekend. The lake has a ton of seaweed and algae resides around the perimeter of the lake. The restaurants are above average and we had a blast at karaoke night. Overall a 4 out of 5!

Reviewed on Jul 10, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,330, price is now CA $1,060 per person
CA $1,060
per person
Sep 11 - Sep 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
The hotel was fantastic! From the champagne upon check-in and records to take to your room, to the live music every night this play was great. The onsite art displays were wonderful and all the staff onsite was friendly and helpful. We would definitely stay here again when we are back in town.

Reviewed on Jul 10, 2026

Comfort Suites Delavan - Lake Geneva Area

Comfort Suites Delavan - Lake Geneva Area

2.5 out of 5
Price was CA $1,563, price is now CA $1,289 per person
CA $1,289
per person
Aug 20 - Aug 25
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Milwaukee (MKE)
8.6/10 Excellent! (1,002 reviews)
Room sizes were great. Staff were very nice. Did not like that the rooms smelled musty.

Reviewed on Jul 8, 2026

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Greendale Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
The price is CA $268 per night from Aug 10 to Aug 11
CA $268
CA $315 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (2,168 reviews)
"Historic"

Reviewed on Jul 11, 2026

The Pfister Hotel
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jul 13 to Jul 14
CA $223
CA $263 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (1,646 reviews)
"Staff very helpful. Loved the bartenders!"

Reviewed on Jul 11, 2026

Potawatomi Hotel & Casino
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
The price is CA $181 per night from Aug 10 to Aug 11
CA $181
CA $214 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (2,313 reviews)
"It was a great place to stay. I wish happy hour was to 8.00pm. We had to work late and it was done by time we got there. Room was really nice and the show was great. The bar / kitchen service was slow. Don't mind waiting on food but 20min to get a drink not good . Over all I would stay there again ..."

Reviewed on Jul 11, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,293 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.
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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 bars while you're in the area.
See properties

What to do in Greendale

Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $118
per adult
Small Group Kayak Tour of Skyline in Milwaukee
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

CA $11
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
See all activities in Greendale

Frequently asked questions

How much does a Greendale vacation package cost?
Offering excellent value package deals from CA $1,040 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?

  1. Pick your travel dates: What you plan to do in Greendale and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.