A lake with autumn foliage, docked boats, and a building on the shore.

Downtown Pewaukee Vacations from $460

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The Latest Downtown Pewaukee Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • An indoor bar area with seating, a fire feature, and a bar stocked with bottles.
    Jan 29 - Feb 1

    Kimpton Journeyman Hotel by IHG + Flight

    Downtown Milwaukee
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • Denver (DEN) - Milwaukee (MKE)
    DEN - MKE • Nonstop MKE - DEN • Nonstop
    $600
    $460
    per traveler
    found 1 day ago
    Kimpton Journeyman Hotel by IHG
  • A grand lobby with ornate columns, a chandelier, and a staircase leading to an upper level.
    Jan 29 - Feb 1

    The Pfister Hotel + Flight

    Downtown Milwaukee
    3 nights
    4.5 star property
    9.6/10 - Exceptional (2,284 reviews)
    "Staff and amenities are always the highlight of staying. A favorite of ours whether it’s for an overnight or weekend away. Truly unique"
    Reviewed November 3, 2026
    Roundtrip • Denver (DEN) - Milwaukee (MKE)
    DEN - MKE • Nonstop MKE - DEN • Nonstop
    $728
    $500
    per traveler
    found 1 day ago
    The Pfister Hotel
  • An outdoor patio area with wicker furniture, hanging plants, and a stone wall backdrop.
    Jan 29 - Feb 1

    The Iron Horse Hotel + Flight

    Fifth Ward
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,398 reviews)
    "Great location and bar! Loved getting a couples massage and a great workout space! It was such a nice quiet area and delicious food near by!"
    Reviewed November 4, 2026
    Roundtrip • Denver (DEN) - Milwaukee (MKE)
    DEN - MKE • Nonstop MKE - DEN • Nonstop
    $616
    $468
    per traveler
    found 1 day ago
    The Iron Horse Hotel
  • A building with a 'Inn' sign, large arched windows, and a well-lit entrance.
    Jan 29 - Feb 1

    Kinn Guesthouse Downtown + Flight

    Downtown Milwaukee
    3 nights
    4.5 star property
    9.4/10 - Exceptional (453 reviews)
    "Very clean and easy to find"
    Reviewed November 4, 2026
    Roundtrip • Denver (DEN) - Milwaukee (MKE)
    DEN - MKE • Nonstop MKE - DEN • Nonstop
    $789
    $617
    per traveler
    found 1 day ago
    Kinn Guesthouse Downtown
  • A busy bar area with multiple shelves stocked with bottles and glasses, a bar counter with a cash register, and a seating area with tables and chairs.
    Jan 29 - Feb 1

    Saint Kate - The Arts Hotel + Flight

    Downtown Milwaukee
    3 nights
    4.0 star property
    9.8/10 - Exceptional (2,743 reviews)
    Roundtrip • Denver (DEN) - Milwaukee (MKE)
    DEN - MKE • Nonstop MKE - DEN • Nonstop
    $685
    $540
    per traveler
    found 1 day ago
    Saint Kate - The Arts Hotel

Where to stay in Downtown Pewaukee

Find the best Downtown Pewaukee areas and neighborhoods for the activities you enjoy most.
A cityscape with a river, green spaces, and modern buildings.

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

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 waterfront cityscape at dusk with a calm river reflecting buildings and a bridge.

Wauwatosa

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 boats, a bridge, and historic buildings along the banks.

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 modern architectural structure with a unique triangular design, a glass facade, and a cable-stayed bridge.

East Town

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

Discover the most popular places to visit in Downtown Pewaukee

Pewaukee Lake Beach

8.2/10 (36 reviews)
If a restful vacation is part of your travel plans, Pewaukee Lake Beach might be the perfect place to seek out during your trip to Pewaukee.
See properties

Downtown Pewaukee Hotel Deals

A room with two metal-framed lounge chairs, one with a towel on it, and a small table with a towel and a rolled-up item.

Holiday Inn Pewaukee - Milwaukee West by IHG

Holiday Inn Pewaukee - Milwaukee West by IHG
3.0 star property
2.7 mi from Downtown Pewaukee
9.0 out of 10, Wonderful, (530 reviews)
"Staff is really helpful, and the place is clean."
$95 nightly
The price is $107
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Pewaukee - Milwaukee West by IHG
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.
See all properties in Downtown Pewaukee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.