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Find Hotels with a Pool in Pewaukee, WI

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Check prices for these dates, December 12 – 13, 2026

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Our top choices for Pewaukee hotels with a pool

1. The Pfister Hotel

An indoor swimming pool with clear views of the cityscape through large windows.

2. Sheraton Milwaukee Brookfield Hotel

An indoor swimming pool with lounge chairs and tables, large windows, and a view of the outside.

3. Drury Plaza Hotel Milwaukee Downtown

A swimming pool with a no diving sign, a chair area, and a stairway leading to the pool.

4. AmericInn by Wyndham Brookfield

An indoor swimming pool with clear glass walls, sun loungers, and a tiled floor.

5. The Ingleside Hotel

A spacious living room with a fireplace, comfortable seating, and a large bookshelf filled with books and decorative items.

6. Embassy Suites by Hilton Milwaukee Brookfield

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a sunbed.

7. Wildwood Lodge

An indoor swimming pool with clear water, surrounded by lounge chairs and a stone-tiled deck.

8. Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

An indoor swimming pool with lounge chairs and umbrellas, surrounded by large windows.

9. Marriott Milwaukee West

A modern lobby with a stone wall, a fireplace, and two yellow armchairs.

10. Best Western Waukesha Grand

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and tables, and large windows offering views of the outdoors.

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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Choose what matters most at hotels with a pool in Pewaukee

Breakfast included

Hot tub

Water park

4 stars

5 stars

Top Pewaukee Hotel Reviews

Holiday Inn Express & Suites Delafield by IHG

An indoor swimming pool with clear water, surrounded by lounge chairs and tables, and large windows offering a view of greenery outside.

Homewood Suites by Hilton Oak Creek Milwaukee

A spacious indoor pool area with a clear view of the pool, seating areas, and a modern ceiling design.

Residence Inn by Marriott Milwaukee Brookfield at Poplar Creek

A large indoor swimming pool with tiled walls and a wooden floor, surrounded by lounge chairs and a small seating area.

The Pfister Hotel

An indoor swimming pool with clear views of the cityscape through large windows.

Residence Inn By Marriott Milwaukee Brookfield

An indoor swimming pool with a high ceiling, large windows, and a seating area.

The Stagecoach Inn Bed & Breakfast and Five20 Social Stop

A garden pathway with potted plants and a stone-tiled walkway.

Marriott Milwaukee West

A modern lobby with a stone wall, a fireplace, and two yellow armchairs.

Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

A modern indoor swimming pool with a lifeguard chair, blue lounge chairs, and a pool lift.

Home2 Suites by Hilton Milwaukee Airport

A swimming pool with a no diving sign, indoor seating area with chairs, and large windows offering a view of trees and buildings.

TownePlace Suites by Marriott Milwaukee Oak Creek

An indoor swimming pool with clear glass walls, a tiled floor, and several chairs and tables around the pool area.

Holiday Inn Pewaukee - Milwaukee West by IHG

An indoor swimming pool with a hot tub, sunlit seating area, and a basketball hoop.

Find out more about Pewaukee

Discover top Pewaukee attractions

Pewaukee offers a delightful blend of natural beauty and engaging activities that will captivate travelers seeking a memorable experience. Begin your adventure at the picturesque Pewaukee Lake, where you can enjoy a serene day of boating or paddleboarding, soaking in the stunning views and tranquility. For those who prefer land-based activities, the scenic trails surrounding the lake provide perfect opportunities for leisurely walks or invigorating bike rides, allowing you to immerse yourself in the area's natural charm. If you're looking for a bit of culture, the local art scene showcases various galleries and studios that feature unique works by talented artists, offering a glimpse into the creative spirit of the community. Additionally, the charming downtown area is filled with boutique shops and artisan stores, where you can find unique souvenirs and gifts to remember your trip. After a day of exploration, unwind at one of the inviting accommodations nearby, where attentive service and comfortable amenities await, ensuring a restful night’s sleep before another day of adventure.

Find the best pool hotels in Pewaukee

For travelers seeking relaxation and fun in the water, Pewaukee offers some excellent hotel options featuring inviting pools. Here are the top selections for a refreshing stay.

Wildwood Lodge

Holiday Inn Pewaukee - Milwaukee West by IHG

Best Western Waukesha Grand

Frequently Asked Questions

What are the best hotels in Pewaukee with outdoor pools?

The Holiday Inn Pewaukee - Milwaukee West by IHG is a fantastic choice for travellers seeking a hotel with an outdoor pool. This 3-star property offers a refreshing outdoor swimming area, ideal for families looking to unwind after a day of adventures.

Guests appreciate the convenience of free WiFi and wired internet, which makes it easy to stay connected while enjoying their stay. The hotel's amenities also include free self-parking, ensuring that you can explore Pewaukee and the surrounding areas without any hassle. With an excellent review rating of 9.0, travellers have consistently praised the overall quality and comfort that this hotel provides, making it a reliable option for those in search of good value.

How much does a hotel with outdoor pool in Pewaukee cost?

Enjoy staying in a hotel in Pewaukee with an outdoor pool. You can find a great deal from $86 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Is it cheaper to book flights and a Pewaukee hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it’s wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Pewaukee for you.

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