Pewaukee Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Hotel Metro, Autograph Collection

Hotel Metro, Autograph Collection

4 out of 5
Downtown Milwaukee
Price was CA $1,370, price is now CA $1,326 per person
CA $1,326
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.2/10 Very good! (1,000 reviews)
This is a beautiful hotel! We were celebrating our anniversary and it was a perfect stay. We stayed in the King room, which was amazing…very large and beautiful. I highly recommend for any occasion.

Reviewed on Oct 22, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,670, price is now CA $1,961 per person
CA $1,961
per person
Dec 13 - Dec 20
found 16 hours ago
Roundtrip flight included
Thunder Bay (YQT) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $2,235, price is now CA $1,757 per person
CA $1,757
per person
Dec 13 - Dec 20
found 16 hours ago
Roundtrip flight included
Thunder Bay (YQT) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,524, price is now CA $1,441 per person
CA $1,441
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (508 reviews)

The Plaza Hotel

The Plaza Hotel

3 out of 5
Downtown Milwaukee
Price was CA $1,479, price is now CA $1,429 per person
CA $1,429
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.8/10 Excellent! (1,258 reviews)

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 $150 per night from Nov 26 to Nov 27
CA $150
CA $170 total
Nov 26 - Nov 27
includes taxes & fees
The Ingleside Hotel
Wildwood Lodge

Wildwood Lodge

2.5 out of 5
N14 W24121 Tower Place Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Nov 24 to Nov 25
CA $110
CA $124 total
Nov 24 - Nov 25
includes taxes & fees
Wildwood Lodge
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 $107 per night from Nov 22 to Nov 23
CA $107
CA $121 total
Nov 22 - Nov 23
includes taxes & fees
Best Western Waukesha Grand
See all 1,283 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.
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Beach Vacations
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Stay near popular Pewaukee attractions

Pewaukee Lake Beach

8.2/10 (36 reviews)
If a restful vacation is part of your travel plans, Pewaukee Lake Beach might be the perfect place to seek out during your trip to Pewaukee.
See properties

What to do in Pewaukee

Milwaukee: Original Ghost Tour

Milwaukee: Original Ghost Tour

CA $69
per adult
Milwaukee: Original Ghost Tour
Milwaukee Historic Downtown Self Guided Walking Tour

Milwaukee Historic Downtown Self Guided Walking Tour

CA $14
per adult
Milwaukee Historic Downtown Self Guided Walking Tour
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

CA $11
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
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 $1,326 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.