Pewaukee Vacation Packages

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Your Pewaukee Vacation

Say bye-bye to the worries of planning and hello to a Pewaukee vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Halls Park, which is good for nature, watersports and views. Fill your free time with visits to Springs Water Park, Pewaukee Lake and Carroll University, some of the attractions you simply have to see during your trip to Pewaukee. Expedia has what you need to escape your daily routine. Tailor your vacation to Pewaukee to suit your style of travel, whatever that may look like.

Top Pewaukee Vacation Deals

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 1 day 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 1 day 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 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.2/10 Very Good! (1,098 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 Pewaukee

Find the best Pewaukee areas and neighborhoods for the activities you enjoy most. Learn more about Pewaukee
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Downtown Pewaukee

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Pewaukee, Pewaukee Lake Beach and Two Brothers Wines are top sights worth seeing.

Find hotels in Downtown Pewaukee

Ready to book your vacation to Pewaukee?

 

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Pewaukee Hotel Deals

The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Aug 10 to Aug 11
CA $133
CA $150 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (667 reviews)
"Very nice staff and clean rooms. Comfortable beds!"

Reviewed on Jul. 31, 2025

The Ingleside Hotel
Best Western Waukesha Grand

Best Western Waukesha Grand

2.5 out of 5
2840 N Grandview Boulevard, Pewaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Aug 10 to Aug 11
CA $106
CA $119 total
Aug 10 - Aug 11
includes taxes & fees
7.8/10 Good! (1,002 reviews)
Dog fee too expensive!!
"I was here for a dog show. $70.00 per dog is too expensive. Special consideration should be made when dog show people are bringing in a lot of money and business to your area."

Reviewed on Aug. 1, 2025

Best Western Waukesha Grand
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
See all 1,419 properties in Pewaukee
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

Discover the most popular places to visit in Pewaukee

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

What to do in Pewaukee

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 Pewaukee

Frequently asked questions

How much does a Pewaukee vacation package cost?
You can pick up a vacation package to this top destination from CA $986 on Expedia. However, how much your vacation to Pewaukee costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Pewaukee?
If you'd like to book a cheap Pewaukee vacation package, consider visiting in January, February and November. You'll generally find better prices on airfares and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Pewaukee?
Dedicate around 2 days for your Pewaukee vacation if you're hoping to discover everything that makes this destination special. Stroll around popular areas, including Starke Peninsula and Five Fields. Then head to the top attractions such as Centre Court Sports Complex and The Corners of Brookfield. With a good itinerary, you can keep busy with room for some rest and relaxation too. Want to travel outside of Pewaukee? Consider a day trip or two.
Is it worth booking a vacation package to Pewaukee?
It's no wonder a Pewaukee vacation is on the must-do list of many travellers. Leading attractions like Pewaukee Lake are just the start of things to keep you busy here.
How to find the best Pewaukee package deals?
Begin your search for a Pewaukee package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Pewaukee package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pewaukee escape off to a flying start.
Is it cheaper to book a Pewaukee vacation as a package?
You can enjoy significant savings on your Pewaukee retreat by booking a personalized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pewaukee?
If you've got your Pewaukee vacation dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Pewaukee?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Pewaukee.
  2. Set your budget: Factor in expenses like transportation, flights and meals when calculating how much to put aside for your trip to Pewaukee. Then, pick a hotel that fits your budget, whether that's a wallet-friendly option or a lavish retreat.
  3. Decide your trip length: Consider how long you want to spend exploring Pewaukee. Plan your days so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: After you've nailed down your dates and duration, book the perfect Pewaukee vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.