Five Fields Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Five Fields

Find the best Five Fields areas and neighborhoods for the activities you enjoy most. Learn more about Five Fields
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Top hotels in Five Fields

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is 4.645.475 ₫ per night from 30 Jan to 31 Jan
4.645.475 ₫
5.477.013 ₫ total
30 Jan - 31 Jan
includes taxes & fees
9.4/10 Exceptional! (1,872 reviews)
The Pfister exceeded my expectations. The staff was exceptional. The entire hotel sparkled.

Reviewed on 11 Jan 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is 3.973.022 ₫ per night from 24 Jan to 25 Jan
3.973.022 ₫
4.684.192 ₫ total
24 Jan - 25 Jan
includes taxes & fees
9.6/10 Exceptional! (2,515 reviews)
Great hotel! So fun and unique. Very clean and personalized

Reviewed on 11 Jan 2026

Saint Kate - The Arts Hotel
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is 3.759.094 ₫ per night from 27 Jan to 28 Jan
3.759.094 ₫
4.431.970 ₫ total
27 Jan - 28 Jan
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Wonderful stay!

Reviewed on 9 Jan 2026

The Iron Horse Hotel
See all 1,195 properties in Five Fields
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.

Frequently asked questions

How much does a Five Fields holiday package cost?
From as low as . Yes, you read that right. Our Five Fields packages are the best way to make your budget stretch further. Combine your flights, hotels and rental car and discover this popular destination.
How do I get a cheap travel package to Five Fields?
Lock in flights that fit in with your schedule, add a hotel room to your booking and watch the savings rack up with a Five Fields holiday package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia is where your cheap holiday begins. And with more than 550 partner airlines and 1null000null000 properties worldwide to pick from, you won't be short of choice.
Where should I stay in Five Fields?
With interesting attractions like Pewaukee Lake Beach and Pewaukee Golf Club in this neighbourhood, try to find a hotel situated near either one. Two Brothers Wines is another sight in Five Fields that draws the crowds.
How far in advance should I book my Five Fields holiday?
Travellers are generally able to look up international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a stroke of luck, it's still possible to purchase an affordable ticket only weeks before your journey.
What does an Expedia Five Fields travel package include?
Hotels, rental cars and flights — we have them well covered. With Expedia, you can shape your Five Fields package the way you want. All you have to do is decide just what you need. Once you've made your booking, you can add on fun things like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Five Fields travel package?
When you book your flights, hotels and car rentals together, you'll pick up awesome discounts. Whether you're planning a rural escape in a cottage or would rather stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Five Fields Expedia holiday package?
Yes, the choice is all yours. Expedia has access to more than 550 airlines across the globe, so you can tailor your Five Fields adventure according to your budget and style.
If I'm not able to travel, can I cancel my Five Fields holiday package?
Don't stress if you're rethinking your Five Fields holiday package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We get that your circumstances can change suddenly, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Popular places to visit

Outfield sign at miller park

American Family Field

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

American Family Field
Harley-Davidson Museum showing interior views

Harley-Davidson Museum

You can spend an afternoon browsing the exhibits at Harley-Davidson Museum in Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Harley-Davidson Museum
Downtown, Milwaukee

Marquette University

Explore the campus of Marquette University during your visit to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Marquette University