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.
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
Price was CA $1,055, price is now CA $923 per person
CA $923
per person
Jun 15 - Jun 18
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.4/10 Very Good! (775 reviews)
Getting here was easy, right off the freeway by the mall. The lobby is nice, and check in was easy. Worth noting to check conferences happening here, was very busy during my stay.

Reviewed on May 5, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,992, price is now CA $1,656 per person
CA $1,656
per person
Jun 15 - Jun 18
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,452 reviews)
I decided on a whim to stay at this hotel instead of closer to my venue. After my stay, I wish I could’ve stayed multiple nights. The room was absolutely gorgeous. I don’t think I’ve ever stayed in as nice as clean or as fancy of a hotel as this room was if I could give it 10 stars, I would definitely five the staff was friendly. The place was extremely clean. The elevators were even friendly as they had a very soothing voice and took me right to the level I needed to just by scanning my badge. I really didn’t wanna leave.

Reviewed on May 8, 2026

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Avenues West
Price was CA $1,558, price is now CA $1,347 per person
CA $1,347
per person
Jun 15 - Jun 18
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9/10 Wonderful! (1,322 reviews)
The bar was great! Reasonable drink prices and 1/2 price apps. The bartender was very friendly. We used the shuttle to go to the Brewers game and that was great! I also felt safe at this property. I liked the gated parking and it was easily accessible. We will stay here again.

Reviewed on May 4, 2026

Home2 Suites by Hilton Milwaukee Downtown

Home2 Suites by Hilton Milwaukee Downtown

3 out of 5
Downtown Milwaukee
Price was CA $1,649, price is now CA $1,438 per person
CA $1,438
per person
Jun 15 - Jun 18
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.6/10 Excellent! (1,002 reviews)
The front desk staff was super friendly and helpful! The room was clean and breakfast far surpassed my expectations!

Reviewed on May 8, 2026

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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 $146 per night from May 11 to May 12
CA $146
CA $165 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (795 reviews)
Very nice update room. Staff very responsive to requests & water and coffee available in the lobby.

Reviewed on May 5, 2026

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 $119 per night from May 24 to May 25
CA $119
CA $135 total
May 24 - May 25
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Great and super friendly/welcoming staff. Definitely went above and beyond being accommodating. They 100% made me feel like I was home and welcomed.

Reviewed on May 7, 2026

Wildwood Lodge
avid hotel Milwaukee West Waukesha by IHG

avid hotel Milwaukee West Waukesha by IHG

2.5 out of 5
2101 Meadow Lane Pewaukee WI
Fully refundable
The price is CA $143 per night from May 24 to May 25
CA $143
CA $162 total
May 24 - May 25
includes taxes & fees
9.4/10 Exceptional! (703 reviews)
Everything was clean and rooms and beds GREAT!

Reviewed on May 5, 2026

avid hotel Milwaukee West Waukesha by IHG
See all 1,335 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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All Inclusive Vacations
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Discover the most popular places to visit in Pewaukee

Harley-Davidson Museum

Harley-Davidson Museum

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

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

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
See all activities in Pewaukee

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