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
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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
Price was CA $1,684, price is now CA $1,112 per person
CA $1,112
per person
Jul 9 - Jul 13
found 21 hours ago
Roundtrip flight included
Detroit (DTT) to Milwaukee (MKE)
9.6/10 Exceptional! (2,115 reviews)
The Pfister Hotel is a lovely place to stay at. It's breathtaking, the food was delicious, very clean, and the staff was fabulous. We enjoyed our time at the lobby enjoying a drink and the music provided by the piano player. I highly recommend The Pfister when visiting Milwaukee/
Reviewed on May 29, 2026
Sheraton Milwaukee Brookfield Hotel
Price was CA $1,495, price is now CA $1,155 per person
CA $1,155
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
8.4/10 Very Good! (814 reviews)
Beautiful decor, clean rooms except there were gnats in the room and from one nights stay, my son had about 9 bug bites on his leg. Also, there’s no microwave in the room.
Reviewed on May 30, 2026
Kinn Guesthouse Bay View
Bay View
Price was CA $1,547, price is now CA $1,205 per person
CA $1,205
per person
Jul 9 - Jul 13
found 21 hours ago
Roundtrip flight included
Detroit (DTT) to Milwaukee (MKE)
9.4/10 Exceptional! (462 reviews)
Kinn Guesthouses are a great place to stay if you don’t mind no front desk and coded entries. We’ve found them to have large rooms which are tastefully decorated, comfortable and quiet. The common area is stocked with teas, coffee and breakfast cereals which you can use.
Be sure to contact property directly before you arrive for entry code. Expedia apparently does not share contact information with Kinn so you can access the room. Therefore they have no way to send you this information This can result in check-in delay until you find a person affiliated with Kinn to update you with this info.
Reviewed on May 29, 2026
The Iron Horse Hotel
Fifth Ward
Price was CA $2,162, price is now CA $1,747 per person
CA $1,747
per person
Jul 9 - Jul 13
found 21 hours ago
Roundtrip flight included
Detroit (DTT) to Milwaukee (MKE)
9.2/10 Wonderful! (1,126 reviews)
Hotel was great! Very unique, artwork, and inside and outdoor dining area was amazing. Room was very roomy and will definitely be back.
Reviewed on May 29, 2026
Greendale Hotel Deals
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jun 2 to Jun 3
CA $205
CA $241 total
Jun 2 - Jun 3
includes taxes & fees
9.2/10 Wonderful! (1,503 reviews)
"Gorgeous hotel and rooms were very nice!!"
Reviewed on May 30, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Jun 21 to Jun 22
CA $261
CA $307 total
Jun 21 - Jun 22
includes taxes & fees
9.6/10 Exceptional! (2,114 reviews)
"The Pfister Hotel is a lovely place to stay at. It's breathtaking, the food was delicious, very clean, and the staff was fabulous. We enjoyed our time at the lobby enjoying a drink and the music provided by the piano player. I highly recommend The Pfister when visiting Milwaukee/"
Reviewed on May 29, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jun 8 to Jun 9
CA $153
CA $177 total
Jun 8 - Jun 9
includes taxes & fees
8.4/10 Very Good! (848 reviews)
"Beautiful decor, clean rooms except there were gnats in the room and from one nights stay, my son had about 9 bug bites on his leg. Also, there’s no microwave in the room."
Reviewed on May 30, 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.
Discover the most popular places to visit in Greendale
Harley-Davidson Museum
Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.
Milwaukee Art Museum
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
Potawatomi Bingo Casino
Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event 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
CA $7
per adult
Small Group Kayak Tour of Skyline in Milwaukee
CA $114
per adult
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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.
