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.
Hampton Inn & Suites Milwaukee Downtown
Westown
Price was CA $1,120, price is now CA $918 per person
CA $918
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Milwaukee (MKE)
6.8/10 (1,009 reviews)
Front desk staff was amazing and the manager welcomed us personally. The hot tub had the best jets I’ve ever experienced in a hotel. Great location - we could walk everywhere.
Reviewed on May 21, 2026
The Pfister Hotel
Downtown Milwaukee
Price was CA $1,336, price is now CA $1,023 per person
CA $1,023
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Milwaukee (MKE)
9.6/10 Exceptional! (2,101 reviews)
I thoroughly enjoyed the staff they were 5* customer service. The bars and restaurant choices were great too.
Reviewed on May 19, 2026
Kinn Guesthouse Bay View
Bay View
Price was CA $1,224, price is now CA $970 per person
CA $970
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Milwaukee (MKE)
9.4/10 Exceptional! (461 reviews)
Love the decor. Felt like home! Walking distance to coffee & dinner places was great!
Reviewed on May 8, 2026
The Brewhouse Inn & Suites
Westown
Price was CA $2,604, price is now CA $2,156 per person
CA $2,156
per person
Aug 6 - Aug 9
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (1,058 reviews)
This was our 4th time staying here and it never disappoints! We love the unique property and rooms, and the fact that there is so much in a walkable distance.
The staff is also wonderful, front desk, valet and restaurant staff. We had fun getting to know Chris in the restaurant/bar.
We will be back!
Reviewed on May 21, 2026
The Iron Horse Hotel
Fifth Ward
Price was CA $1,965, price is now CA $1,642 per person
CA $1,642
per person
Aug 6 - Aug 9
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,111 reviews)
This is probably one of the most beautiful iconic historical hotels you will see. The artwork alone is like being in an art show. The architecture, the industrial feel, plus all the motorcycle and vintage merchandise. I've traveled quite a bit and I've never seen anything quite like it. Amazing, fantastic, beautiful, inspiring, iconic, fun, historical, and good food and drinks. You won't be disappointed.
Reviewed on May 19, 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 May 25 to May 26
CA $205
CA $242 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (1,484 reviews)
"Haven’t been there in years! Many things have changed! Nice casino and hotel!"
Reviewed on May 20, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Jun 14 to Jun 15
CA $234
CA $276 total
Jun 14 - Jun 15
includes taxes & fees
9.6/10 Exceptional! (2,104 reviews)
"Historic"
Reviewed on May 20, 2026
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from May 25 to May 26
CA $285
CA $336 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (1,133 reviews)
"DO NOT STAY HERE. Someone broke into our room, flooded the bathroom sink, and the hotel charged me $250 while refusing to return my calls. On 5/15 left our room with the do not disturb sign on the door. When we returned, our belongings had clearly been moved around and the toilet paper was soaked. ..."
Reviewed on May 20, 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
5/5(13 reviews)
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
5/5(12 reviews)
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
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.
