Downtown Pewaukee Vacation Packages 2026 from $508

The Latest Downtown Pewaukee Vacation Packages

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

Kinn Guesthouse Bay View

Bay View

$508

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.4/10 Exceptional! (496 reviews)

Great Location. Nice restaurant in building.

Reviewed on Aug 20, 2026

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$679

per person

Oct 29 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.6/10 Exceptional! (2,221 reviews)

The Iron Horse Hotel

Fifth Ward

$534

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.2/10 Wonderful! (1,291 reviews)

We loved the Iron Horse Hotel! It was very clean, beautiful and perfect in every way. We liked that we could walk to the HD museum and that we could park our motorcycles for free. We loved the restaurant.

Reviewed on Aug 22, 2026

Saint Kate - The Arts Hotel

Downtown Milwaukee

$680

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.8/10 Exceptional! (2,658 reviews)

Love the themed rooms and hotel. Really comfortable rooms (with Victrola record players and record albums!!!). Onsite art museum. Excellent complimentary champagne upon checking in!!! Only disappointment is that the Studio Restaurant has ridiculous open/close hours. Plan accordingly! With that exception, definitely a new and fun place to return to. Btw, Pabst Theater is located within the building. 5 min walk from the lobby!! Super convenient!!

Reviewed on Aug 22, 2026

Kinn Guesthouse Downtown

Downtown Milwaukee

$669

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.4/10 Exceptional! (391 reviews)

Every person we were with, had a problem with access codes. That became really annoying.

Reviewed on Aug 22, 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 river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

1 out of top 10 points of interest in this area

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 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 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.

A boat named "Vista King" on a river with a building featuring fish decorations in the background.

Westown

2 out of top 10 points of interest in this area

While visiting Westown, you might make a stop by sights like Miller High Life Theatre and UW–Milwaukee Panther Arena.

Downtown Pewaukee Hotel Deals

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$80 nightly

$93 total

Aug 24 - Aug 25

Total with taxes and fees

8/10 Very Good! (1,526 reviews)

"Room was better than expected, property well maintained. Breakfast was ok -- regular coffee was not working, yet had 2 personal coffee in the room - which was fine. Pool was good, although smaller than we hoped -- I call it a bonus either way. I'd go back to the place."

Reviewed on Aug 23, 2026

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

$159 nightly

$188 total

Sep 13 - Sep 14

Total with taxes and fees

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$81 nightly

$94 total

Aug 30 - Aug 31

Total with taxes and fees

8.4/10 Very Good! (1,130 reviews)

"Thermostat in our room did not work so air conditioning stayed on whole time and room did not get above 65 degrees. Remote batteries didn’t work took a bit for someone to come give us new oned"

Reviewed on Aug 22, 2026

See all 1,137 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.