Five Fields Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Five Fields

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Milwaukee South by IHG

Crowne Plaza Milwaukee South by IHG

3.5 out of 5
College Heights
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.2/10 Very Good! (1,000 reviews)
Staff was kind, our first room was 86 degrees when we checked in around 6pm and the AC didn’t seem to work well within the hour so we asked for another room as our toddler was nearing bedtime and we also had an infant. We did get moved to another room that was much cooler so that was resolved. The beds were comfy, it’s definitely not a premium hotel but it worked for the night with an early morning flight. Shuttle was convenient but the driver wasn’t even near the shuttle until 558am with a 6am scheduled departure. Staff didn’t relay to us shuttle times when we initially asked about it upon check-in but it worked out and was a short drive.

Reviewed on Aug. 2, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (1,659 reviews)
A great experience!

Reviewed on Jul. 31, 2025

Hilton Milwaukee

Hilton Milwaukee

4 out of 5
Westown
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.2/10 Very Good! (1,106 reviews)
Rooms could of been cleaner stain on carpet maybe vacuum better very spacious nice bed

Reviewed on Jul. 29, 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

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 CA $255 per night from Aug 28 to Aug 29
CA $255
CA $301 total
Aug 28 - Aug 29
includes taxes & fees
9.4/10 Exceptional! (1,681 reviews)
"A great experience!"

Reviewed on Jul. 31, 2025

The Pfister Hotel
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Aug 4 to Aug 5
CA $200
CA $236 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,357 reviews)
"Free valet"

Reviewed on Aug. 1, 2025

Potawatomi Hotel & Casino
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Aug 10 to Aug 11
CA $120
CA $139 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (357 reviews)
"Enjoy my stay"

Reviewed on Jul. 30, 2025

Sheraton Milwaukee Brookfield Hotel
See all 1,344 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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Five Fields vacation package cost?
From as low as CA $986. 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 vacation package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia is where your cheap vacation begins. And with more than 550 partner airlines and 1,000,000 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 neighborhood, 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 vacation?
Travelers 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 vacation 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 vacation package?
Don't stress if you're rethinking your Five Fields vacation 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.

Discover the most popular places to visit in Five Fields

Harley-Davidson Museum featuring interior views

Harley-Davidson Museum

5/5(13 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 Art Museum

Milwaukee Art Museum

5/5(12 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

Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Potawatomi Bingo Casino

Things to do

Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $114
per adult
Small Group Kayak Tour of Skyline in Milwaukee
Kayaks Rentals Everyday

Milwaukee Kayak Rental

CA $75
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.