Five Fields Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Packages with flights are ATOL protected

Your Five Fields Holiday

Your next great escape beckons with a holiday package to Five Fields. Entertainment, relaxation and nothing but great times — you're sure to find it in this neighbourhood. Want to sightsee during your trip to Five Fields? Don't miss nearby attractions like Pewaukee Lake Beach, Pewaukee Golf Club and Two Brothers Wines. Don't just imagine it — make it happen! Book your ultimate Five Fields holiday with Expedia and travel your way.

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
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Cathedral Square 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

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is £74 per night from 9 Nov to 10 Nov
£74
9 Nov - 10 Nov
includes taxes & fees
Hyatt Regency Milwaukee
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 £75 per night from 8 Nov to 9 Nov
£75
8 Nov - 9 Nov
includes taxes & fees
Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
The price is £105 per night from 2 Nov to 3 Nov
£105
2 Nov - 3 Nov
includes taxes & fees
9.6/10 Exceptional! (2,429 reviews)
"Was a fantastic place in a great location. Would stay again without question!"

Reviewed on 27 Oct 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,235 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Five Fields travel package cost?
The cheapest Five Fields package is , so your dream escape can become a reality — without the high price tag. Bundle flights, hotels, car rentals and more to build a package that fits you.
If I'm not able to travel, can I cancel my Five Fields travel package?
We totally understand that sometimes life doesn't go according to plan. If you've locked in a Five Fields travel package and need to cancel or change it, we can help. It's always worth looking up our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it's been longer than 24 hours, your airline, hotel or car rental company may charge a fee.
How do I get a cheap travel package to Five Fields?
Bundle, bundle, bundle. Flights, hotels and rental cars — combine whatever you need into a Five Fields travel package to save loads of cash. Score even more bargains when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to customize your trip your own way. We offer more than 550 air carriers and 1,000,000 hotel options around the world, so that everyone has an opportunity to travel and fulfil those holiday dreams.
Does Expedia offer Book Now, Pay Later Five Fields holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a terrific getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that suit all budgets, so you can book that well-deserved holiday sooner.
  • Pay in instalments holidays: If you'd like to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan from Klarna.

Where should I stay in Five Fields?
A holiday in Five Fields isn't complete without checking out Pewaukee Lake Beach. Why not stay close to this great attraction?
What are the top hotels in Five Fields?
Get your holiday off to a flying start by staying at Best Western Waukesha Grand. It's one of most popular hotels in Five Fields. Another comfortable option is The Ingleside Hotel.
How far in advance should I book my Five Fields holiday?
Travellers can normally look up international flights on Expedia up to 12 months prior to departure. Booking last minute? With a little bit of luck, it's still possible to score a cheaper ticket only weeks before your flight.
What does an Expedia Five Fields travel package include?
Packages include hotels, rental cars and flights, but you can combine any of them to create your ideal Five Fields getaway. You can also add on some activities and experiences once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Five Fields travel package?
An Expedia travel package can be customized for your circumstances and is a fantastic way to make your money go further. How little or much you include is totally up to you. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a Five Fields Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

Things to do

Grohmann Museum

Skip the Line: Museum Admission Ticket - Grohmann Museum

£4
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

£19
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

£12
per adult
Downtown Milwaukee 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. Flight-inclusive packages are ATOL protected.