Possibility Playground Flight + Hotel Packages

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

Staybridge Suites Milwaukee Airport South by IHG

$636

per person

Jul 8 - Jul 12

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Franklin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Milwaukee County Sport Complex and Rock Snow Park are located nearby.

Wildwood Lodge

$753

per person

Jul 14 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Pewaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions K1 Speed and Center Court Sports Complex are located nearby.

Hampton Inn & Suites Milwaukee West

$963

per person

Jul 14 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and American Family Field are located nearby.

Home2 Suites By Hilton Milwaukee West

$947

per person

Jul 14 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Milwaukee (MKE)

Stay at this hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Milwaukee County Zoo are located nearby.

Hampton Inn by Hilton Milwaukee Northwest

$716

per person

Jul 14 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and The Mayfair Collection are located nearby.

Dubbel Dutch

$787

per person

Jul 8 - Jul 12

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

Stay at this hotel in Milwaukee. Enjoy free WiFi, parking (surcharge), and housekeeping. Popular attractions Henry W. Maier Festival Park and Fiserv Forum are located nearby.

The Iron Horse Hotel

$897

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harley-Davidson Museum and Henry W. Maier Festival Park are located nearby.

Kinn Guesthouse Bay View

$859

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Our guests praise the clean rooms in our reviews. Popular attractions Henry W. Maier Festival Park and Harley-Davidson Museum are located nearby.

Washington House Inn

$1,118

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Stay at this B&B in Cedarburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Amy's Candy Kitchen and Cedar Creek Settlement are located nearby.

Candlewood Suites Milwaukee Airport by IHG

$639

per person

Jul 8 - Jul 12

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Oak Creek. Enjoy free WiFi, free parking, and a free airport shuttle. Our guests praise the helpful staff in our reviews. Popular attractions South Milwaukee Performing Arts Center and South Milwaukee Downtown Market are located nearby.

Hyatt Regency Milwaukee

$698

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.

The Brewhouse Inn & Suites

$810

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.

3-4 Night Vacations in Possibility Playground

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

Dubbel Dutch

Downtown Milwaukee

$787

per person

Jul 8 - Jul 12

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

The Iron Horse Hotel

Fifth Ward

$897

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Kinn Guesthouse Bay View

Bay View

$859

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

Washington House Inn

$1,118

per person

Jul 14 - Jul 18

found 10 hours ago

Roundtrip flight included

Nashville (BNA) to Milwaukee (MKE)

5-7 Night Vacations in Possibility Playground

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