Downtown Pewaukee Vacation Packages

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Top Holiday Package Deals in Downtown Pewaukee

Price found within the past 48 hours. Click for updated prices.

The Ingleside Hotel

CA $979

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

8.6/10 Excellent! (927 reviews)

The Pfister Hotel

Downtown Milwaukee

CA $1,163

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.6/10 Exceptional! (2,244 reviews)

The Iron Horse Hotel

Fifth Ward

CA $1,211

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.2/10 Wonderful! (1,310 reviews)

Saint Kate - The Arts Hotel

Downtown Milwaukee

CA $1,151

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.8/10 Exceptional! (2,674 reviews)

Dubbel Dutch

Downtown Milwaukee

CA $1,084

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Milwaukee (MKE)

9.2/10 Wonderful! (185 reviews)

Nice place. Great location. Good price. Convenient though pricey parking. Rooms very dark and bathroom sparsely furnished. Staff a little slow to get us check in codes.

Reviewed on Sep 17, 2026

Where to stay in Downtown Pewaukee

Find the best Downtown Pewaukee areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Pewaukee

A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

A stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

1 out of top 10 points of interest in this area

Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.

A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

A pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

East Town

East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.

Downtown Pewaukee Hotel Deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $271

CA $320 total

Sep 20 - Sep 21

includes taxes & fees

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

CA $110

CA $127 total

Sep 20 - Sep 21

includes taxes & fees

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

CA $130

CA $153 total

Sep 29 - Sep 30

includes taxes & fees

8.6/10 Excellent! (1,467 reviews)

"Clean, decent looking hotel. Connects directly to the Baird. Friendly helpful staff. Cons...in room phone didn't work...so when non working toilet didn't work and needed an extra pillow, had to go downstairs to notify them. Also, my key card/fob didn't work about 4 times, yup, another trip downstairs. ..."

Reviewed on Sep 18, 2026

See all 1,113 properties in Downtown Pewaukee

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.