Downtown Pewaukee Vacation Packages 2026 from $740

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Downtown Pewaukee Vacation Packages

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

Landing Apartments at Mayfair Collection

Wauwatosa

$740

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

10/10 Exceptional! (4 reviews)

Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!

Reviewed on May 21, 2026

The Iron Horse Hotel

Fifth Ward

$767

per person

Oct 28 - Nov 2

found 1 day ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.2/10 Wonderful! (1,310 reviews)

The Pfister Hotel

Downtown Milwaukee

$938

per person

Nov 29 - Dec 4

found 21 hours ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.6/10 Exceptional! (2,244 reviews)

Saint Kate - The Arts Hotel

Downtown Milwaukee

$887

per person

Nov 29 - Dec 4

found 21 hours ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.8/10 Exceptional! (2,674 reviews)

Kinn Guesthouse Downtown

Downtown Milwaukee

$997

per person

Nov 29 - Dec 4

found 21 hours ago

Roundtrip flight included

Denver (DEN) to Milwaukee (MKE)

9.4/10 Exceptional! (412 reviews)

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

$194 nightly

$229 total

Oct 19 - Oct 20

Total with taxes and fees

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Fully refundableReserve now, pay when you stay

$78 nightly

$90 total

Sep 20 - Sep 21

Total with taxes and fees

8/10 Very Good! (1,597 reviews)

"I stay at this hotel a couple of times a month and the rooms need an upgrade - - mainly the bathroom. There have been a few hairs on the walls of the tub/shower."

Reviewed on Sep 16, 2026

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

$93 nightly

$110 total

Sep 29 - Sep 30

Total with taxes and fees

See all 1,122 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.