Waukesha Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to SAR 390 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

Find the Best Waukesha Vacation Packages

Waukesha Hotel Deals

Tru By Hilton Milwaukee Brookfield
Tru By Hilton Milwaukee Brookfield
2.5 out of 5
20925 Watertown Road, Waukesha, WI
Fully refundableReserve now, pay when you stay
The price is SAR 316 per night from Apr 10 to Apr 11
SAR 316
SAR 357 total
includes taxes & fees
10 Apr - 11 Apr
8.8/10 Excellent! (626 reviews)
"Very well kept property. Staff Excellent. Wil stay again and will recommend to anyone visiting Waukesha."

Reviewed on 30 March 2025

Tru By Hilton Milwaukee Brookfield
Drury Plaza Hotel Milwaukee Downtown
Drury Plaza Hotel Milwaukee Downtown
3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is SAR 416 per night from Apr 7 to Apr 8
SAR 416
SAR 491 total
includes taxes & fees
7 Apr - 8 Apr
9.6/10 Exceptional! (1,673 reviews)
"Liked everything about the place. Breakfast was good kickback dinner was great!"

Reviewed on 31 March 2025

Drury Plaza Hotel Milwaukee Downtown
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 SAR 708 per night from Apr 20 to Apr 21
SAR 708
SAR 835 total
includes taxes & fees
20 Apr - 21 Apr
9.4/10 Exceptional! (1,627 reviews)
Out of this world experience.
"This was one of the most beautiful hotels that I have ever stayed at. The staff were incredible. I highly recommend the experience!"

Reviewed on 30 March 2025

The Pfister Hotel
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 Waukesha vacation package cost?
Offering excellent value package deals on Expedia, you’ll be surprised at how little a vacation to Waukesha costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Waukesha?
January, February and November are great times to look for cheap Waukesha vacation packages. Choosing to travel in less busy months means you can usually find reduced prices on flights and accommodations.
How to find the best Waukesha package deals?
Start your search for a Waukesha package deal by entering your preferred travel dates and destination under our “Packages” tab. Then add some filters, like “Guest rating” and “Property type,” to tailor the results to your exact needs. You can also sort by “Package discount” and discover offers that come with big savings. If you don’t find the perfect Waukesha package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Waukesha adventure underway.
Is it cheaper to book a Waukesha vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You’ll usually land a better deal than booking each component separately. And you’ll still have the flexibility to create a tailored Waukesha vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Waukesha?
If you’re planning an impromptu Waukesha vacation, check out our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Waukesha?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Waukesha.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and experiences. Your hotel will probably be the biggest expense during your trip to Waukesha.
  3. Decide your trip length: Consider how much time you want to spend exploring Waukesha. Plan your itinerary so you can get to all the activities and attractions you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Waukesha vacation package.

Discover the most popular places to visit in Waukesha