Pewaukee Vacation Packages 2026 from $538

Pewaukee flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

The Ingleside Hotel

$538

per person

Nov 25 - Nov 28

found 16 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Milwaukee (MKE)

A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.

The Iron Horse Hotel

Fifth Ward

$591

per person

Nov 25 - Nov 28

found 16 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Milwaukee (MKE)

This boutique hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. WiFi in public areas is free.

The Pfister Hotel

Downtown Milwaukee

$717

per person

Nov 25 - Nov 28

found 16 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

Saint Kate - The Arts Hotel

Downtown Milwaukee

$755

per person

Nov 25 - Nov 28

found 16 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Milwaukee (MKE)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

County Clare Irish Hotel & Pub

Downtown Milwaukee

$611

per person

Nov 25 - Nov 28

found 16 hours ago

Roundtrip non-stop flight included

Washington (IAD) to Milwaukee (MKE)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking. Dry cleaning and luggage storage are also provided.

Top Pewaukee hotels deals

Wildwood Lodge

N14 W24121 Tower Place Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$102 total

Nov 2 - Nov 3

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Ingleside Hotel

2810 Golf Road Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Oct 22 - Oct 23

Total with taxes and fees

Pool

Pet friendly

Best Western Waukesha Grand

2840 N Grandview Boulevard Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$79 nightly

$89 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Pool

Hot Tub

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$99 total

Nov 9 - Nov 10

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.

Pet friendly

Free WiFi

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.

Pool

Hot Tub

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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.

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

Frequently asked questions

How much are vacation packages to Pewaukee?

Prepare to be pleasantly surprised — you can unwind in Pewaukee for just $538. Here at Travelocity, we save you time and money with our awesome vacation package deals. With flights, hotels and experiences all ready to be snapped up, why put it off?

How long should my Pewaukee vacation be?

Many travelers lock in a hotel for 2 nights in Pewaukee. But that doesn't mean you have to follow in their footsteps. How long you choose to stay all comes down to what sorts of things you want to do on your vacation. If you want to familiarize yourself with every inch of this wonderful destination, stay another few nights (or even longer!).

Where can I get the best vacation package deals for Pewaukee?

There are incredible Pewaukee package deals to be gained with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the world? Remember this the next time you're ready to check another place off your must-visit list.

Why should I book my Pewaukee vacation bundle via Travelocity?

Nothing beats the satisfaction of knowing you've just scored the best price around — that's our Price Match Guarantee. Add to that our incredibly broad range of magical destinations and 24/7 team of customer service professionals and you've got the formula for a hassle-free vacation.

Will I save money on my Pewaukee car rental if I combine it with a hotel or flight?

You most certainly can — bundle your hotel, car and flight into a Pewaukee vacation package and you'll save tons. With so many places to explore in the Pewaukee area, having your own ride will more than come in handy. Once you're in the driver's seat, turn up the stereo and head toward Wrigley Field, a top attraction around 85 mi from Pewaukee.

Which airport is best for Pewaukee?

General Mitchell Intl. Airport (MKE), 20 mi southeast of the city center, is where many visitors begin their adventures in Pewaukee. But it's possible that Dane County Regional Airport (MSN) (55 mi away from central Pewaukee) could be more convenient for you.

What is there to do in Pewaukee?

Pewaukee is full of places to explore, such as Pewaukee Lake and Pewaukee Lake Beach. These two fantastic attractions are at the top of most people's must-see lists.

Where should I stay when visiting Pewaukee?

Many visitors stay at the Best Western Waukesha Grand. It's an excellent base for your Pewaukee escape.