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Hillside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 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 (1,364 reviews)
    "Didn’t like that the power went out"
    Reviewed August 5, 2026
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,005
    CA $890
    per traveller
    found 13 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 13 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 13 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 13 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 (1,723 reviews)
    "People and staff were courteous and polite. Unfortunately air conditioning in the room didn’t work and poor sleep."
    Reviewed August 5, 2026
    Roundtrip • Burlington (BTV) - Milwaukee (MKE)
    BTV - MKE • 1 stop MKE - BTV • 1 stop
    CA $1,111
    CA $994
    per traveller
    found 13 hours ago
    Potawatomi Hotel & Casino
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.