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Port Washington Vacation Packages

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Port Washington Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Price was $677, price is now $526 per person
$526
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 American Family Field and Henry W. Maier Festival Park are located nearby.

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Price was $801, price is now $589 per person
$589
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Harley-Davidson Museum are located nearby.

Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
Price was $720, price is now $546 per person
$546
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
Book a stay at this golf hotel in Brookfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Wisconsin State Fair Park are located nearby.
It’s a nice clean place to stay in Brookfield!

Reviewed on Sep 14, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Price was $820, price is now $625 per person
$625
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions American Family Field and Harley-Davidson Museum are located nearby.

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Price was $747, price is now $569 per person
$569
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
We loved this hotel and want to come back to explore all of the amazing art installations. Our room was one of a kind with interesting decor and original artwork on the walls. Fabulous lobby bar serving food and hosting nighttime entertainment. We were 7 minutes walk to Fiserv arena to see Eric Clapton. The surrounding area is beautiful. Right next to the Riverwalk. Can’t wait to return.

Reviewed on Sep 14, 2026

Dubbel Dutch

Dubbel Dutch

3 out of 5
Price was $678, price is now $528 per person
$528
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free WiFi, parking (surcharge), and housekeeping. Popular attractions American Family Field and Fiserv Forum are located nearby.
This is a nice boutique hotel. It’s a low key setup with no front desk. However, staff is very responsive. They are available by text/call. We loved the experience at the Agency cocktail lounge.

Reviewed on Sep 10, 2026

The Ingleside Hotel

The Ingleside Hotel

4 out of 5
Price was $821, price is now $640 per person
$640
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Springs Water Park and Pewaukee Golf Club are located nearby.
The staff was really polite, the room was clean but it smelled of weed so badly. Everytime you stepped outside of your room it was an instant headache. Everything else was good.

Reviewed on Sep 14, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $741, price is now $591 per person
$591
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and 7 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Potawatomi Bingo Casino are located nearby.

Port Washington Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $747, price is now $569 per person
$569
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,246, price is now $731 per person
$731
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Kansas City (MCI) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $802, price is now $589 per person
$589
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Milwaukee (MKE)
Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $820, price is now $625 per person
$625
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)

Port Washington Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Milwaukee Airport by IHG

Candlewood Suites Milwaukee Airport by IHG

2.5 out of 5
Price was $737, price is now $496 per person
$496
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,388, price is now $857 per person
$857
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $1,335, price is now $875 per person
$875
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,524, price is now $1,134 per person
$1,134
per person
Nov 26 - Dec 3
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Oct 15 - Tue, Oct 20
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$166 Roundtrip, found 3 hours ago
$166
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Oct 15 from Orlando Intl. to General Mitchell Intl., returning Tue, Oct 20, priced at $166 found 3 hours ago
Sun Country Airlines
Thu, Oct 1 - Sun, Oct 4
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Oct 1 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Oct 4, priced at $200 found 1 day ago
Bargain Flight
Sat, Nov 14 - Sat, Dec 5
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$228 Roundtrip, just found
$228
Roundtrip
just found
Select Bargain Flight flight, departing Sat, Nov 14 from Hartsfield-Jackson Atlanta Intl. to General Mitchell Intl., returning Sat, Dec 5, priced at $228 just found
Southwest Airlines
Tue, Oct 27 - Wed, Oct 28
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$237 Roundtrip, found 12 hours ago
$237
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Sky Harbor Intl. to General Mitchell Intl., returning Wed, Oct 28, priced at $237 found 12 hours ago