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Hillside Vacation Packages

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The Latest Hillside Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sept 11 - Sept 14

    Ambassador Hotel Milwaukee, Trademark Collection by Wyndham + Flight

    Marquette
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,365 reviews)
    "Enjoyed our stay as the staff was very cordial and helpful. Liked that there is a shuttle available to most venues. Rooms were clean and comfortable."
    Reviewed August 6, 2026
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,005
    CA $890
    per traveller
    found 19 hours ago
    Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
  • Lobby
    Sept 11 - Sept 14

    The Pfister Hotel + Flight

    Downtown Milwaukee
    3 nights
    4.5 star property
    9.6/10 - Exceptional (2,204 reviews)
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $2,010
    CA $1,440
    per traveller
    found 19 hours ago
    The Pfister Hotel
  • Deluxe King
    Sept 11 - Sept 14

    Saint Kate - The Arts Hotel + Flight

    Downtown Milwaukee
    3 nights
    4.0 star property
    9.8/10 - Exceptional (2,659 reviews)
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,371
    CA $1,092
    per traveller
    found 19 hours ago
    Saint Kate - The Arts Hotel
  • 2 restaurants; lunch and dinner served
    Sept 11 - Sept 14

    The Iron Horse Hotel + Flight

    Fifth Ward
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,271 reviews)
    "The outdoor bar is glorious! Comfy beds, nice staff!"
    Reviewed August 5, 2026
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,427
    CA $1,156
    per traveller
    found 19 hours ago
    The Iron Horse Hotel
  • Aerial view
    Sept 11 - Sept 14

    Potawatomi Hotel & Casino + Flight

    Menomonee River Valley
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,725 reviews)
    "A fart as Casino/Hotels go, this is one of the best I've been to. Very nice rooms."
    Reviewed August 6, 2026
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,111
    CA $994
    per traveller
    found 19 hours ago
    Potawatomi Hotel & Casino