Maitland Park Vacation Packages

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Top Holiday Package Deals in Maitland Park

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

Saint Kate - The Arts Hotel

Downtown Milwaukee
CA $644
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Milwaukee (MKE)
9.8/10 Exceptional! (2,725 reviews)
Wonderful unique hotel, with great good, very helpful and friendly staff. The rooms are gorgeous with quirky art and decorations. Room was spacious and bed very comfortable. Wish I could have stayed longer.

Reviewed on Oct 6, 2026

The Pfister Hotel

The Pfister Hotel

Downtown Milwaukee
CA $762
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Milwaukee (MKE)
9.6/10 Exceptional! (2,283 reviews)
Great historic hotel. Enjoyed with my family

Reviewed on Oct 7, 2026

The Iron Horse Hotel

The Iron Horse Hotel

Fifth Ward
CA $650
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Milwaukee (MKE)
9.2/10 Wonderful! (1,353 reviews)
Just had an excellent stay at the Iron Horse, which has always been one of my favorite places to stay in Milwaukee, despite it's somewhat off the beaten path location. It's been a few years since I've stayed there, and as someone who follows the Milwaukee business environement closely from afar, I know the hotel has had a very rough last few years since covid from a financial, legal, ownership and management perspective. From what I understand, those issues have now largely been resolved, and my guest experience was as good as I remembered. Very large clean rooms, daily housekeeping, and great service from the front desk staff. The lobby is large, open and inviting with very comfortable plush leather furniture and ample room to work and fire up a laptop if need be, The only noticeable difference from when I stayed there last is that it doesn't seem to be quite as "happening" of a venue as it once was. The bar and restaurant just off of the lobby used to be quite the scene a few years back, but neither were very crowded at all during my stay. Still, the guest experience was excellent and I can confidently say it's still one of my favorite properties to stay in the city.

Reviewed on Oct 8, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

Downtown Milwaukee
CA $913
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Milwaukee (MKE)
9.4/10 Exceptional! (432 reviews)
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

Menomonee River Valley
CA $715
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Milwaukee (MKE)
9.2/10 Wonderful! (1,808 reviews)

Where to stay in Maitland Park

Find the best Maitland Park areas and neighborhoods for the activities you enjoy most. Learn more about Maitland Park
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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 stone bridge with a wooden walkway surrounded by lush greenery.

Wauwatosa

1 out of top 10 points of interest in this area

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 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 river with boats, a marina, and historic buildings along the waterfront.

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 pedestrian bridge over a river with a city skyline in the background, including a prominent bank building.

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.

Maitland Park Hotel Deals

Country Inn & Suites by Radisson, Milwaukee Airport, WI

Country Inn & Suites by Radisson, Milwaukee Airport, WI

6200 S 13th St Milwaukee WI
Fully refundable
CA $99
CA $117 total
Nov 1 - Nov 2
includes taxes & fees
Country Inn & Suites by Radisson, Milwaukee Airport, WI
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
CA $133
CA $156 total
Nov 1 - Nov 2
includes taxes & fees
Hyatt Regency Milwaukee
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
CA $91
CA $105 total
Nov 1 - Nov 2
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
See all 1,245 properties in Maitland Park
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.

Things to do

View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

CA $22
per adult
Downtown Milwaukee Walking Tour
Historic Third Ward Walking Tour

Historic Third Ward Walking Tour

CA $22
per adult
Historic Third Ward Walking Tour
Milwaukee's Riverwalk Walking Tour

Milwaukee's Riverwalk Walking Tour

CA $22
per adult
100% of travellers recommend
Milwaukee's Riverwalk Walking Tour
See all activities in Milwaukee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.