Five Fields Vacations from $282

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Your Five Fields Vacation

Planning your next adventure just got a whole lot easier with a vacation package to Five Fields. Take in the very best this neighborhood has to offer while making beautiful memories you'll remember for years. Your trip to Five Fields wouldn't be complete without exploring popular attractions nearby such as Pewaukee Lake Beach, Pewaukee Golf Club and Two Brothers Wines. Stop dreaming and start doing. When you're ready to book your ideal vacation to Five Fields, Expedia will help get you there.

The Latest Five Fields Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Milwaukee-West Medical Center by IHG

Holiday Inn Express Milwaukee-West Medical Center by IHG

2.5 out of 5
Wauwatosa
Price was $366, price is now $282 per person
$282
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
7.8/10 Good! (1,000 reviews)
The room was very nice and clean. The parking is a little tight if you have a truck.

Reviewed on Aug 25, 2025

DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was $457, price is now $327 per person
$327
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
8.4/10 Very Good! (1,002 reviews)
It was a wonderful experience. The staff was super friendly and kind. We found it kid friendly and felt safe.

Reviewed on Aug 15, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was $566, price is now $416 per person
$416
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Amazing night front desk staff!

Reviewed on Aug 26, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $619, price is now $467 per person
$467
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (1,698 reviews)
This is a great property to stay at, the hotel is very nice with lots of artwork and ambience. I highly recommend if you’re ever in Milwaukee..

Reviewed on Aug 23, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $598, price is now $461 per person
$461
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.2/10 Wonderful! (1,011 reviews)
Always an enjoyable stay @The Ironhorse.. Beds are uber comfortable , love the pillows !

Reviewed on Aug 27, 2025

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
Milwaukee

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.

Find hotels in Downtown Milwaukee

Five Fields Hotel Deals

Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 4 to Sep 5
$107 total
Sep 4 - Sep 5
Total with taxes and fees
7.4/10 Good! (1,601 reviews)
"It was actually very comfortable bed needs some updates but still very clean people at the desk were awesome!"

Reviewed on Aug 24, 2025

Sonesta Milwaukee West Wauwatosa
AmericInn by Wyndham Glendale/Milwaukee

AmericInn by Wyndham Glendale/Milwaukee

2.5 out of 5
5110 N Port Washington Rd, (772), Milwaukee, WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $78 total per night from Sep 14 to Sep 15
$78 total
Sep 14 - Sep 15
Total with taxes and fees
7.6/10 Good! (1,014 reviews)
"Good breakfast. Convenient to where we were visiting."

Reviewed on Aug 24, 2025

AmericInn by Wyndham Glendale/Milwaukee
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $97 total per night from Sep 17 to Sep 18
$97 total
Sep 17 - Sep 18
Total with taxes and fees
8/10 Very Good! (1,268 reviews)
Great value for good accommodations!
"The room and facilities are well kept and pleasant. The front desk staff are friendly and go out of their way to be helpful. The price for the conditions and service is low compared to nearby hotels. The breakfast provided is limited."

Reviewed on Aug 25, 2025

Sonesta Select Milwaukee Brookfield
See all 1,289 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Five Fields

Harley-Davidson Museum showing interior views

Harley-Davidson Museum

4.5/5(337 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Harley-Davidson Museum
Milwaukee County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

4.5/5(217 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo
Milwaukee Art Museum

Milwaukee Art Museum

4.5/5(400 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Milwaukee Art Museum

Things to do

At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

$26
per adult
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
The Grand Walk: A Self-Guided Audio Tour through Milwaukee

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

$9
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
Kayaks Rentals Everyday

Milwaukee Kayak Rental

$55
per adult
Milwaukee Kayak Rental
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.