When is the best time to go to Hillside?

The best time to visit Hillside, Wisconsin, is during the summer months, from June to August, and for the autumn colours in September and October. Summer offers the warmest weather, great for enjoying Hillside's outdoor activities. The lake is ideal for swimming, boating, and fishing, and the surrounding trails are excellent for hiking and cycling. Many local events and farmers' markets take place during this season, creating a lively option around the town square. This is a great time for families looking to make the most of the long daylight hours and recreational opportunities. For those who appreciate natural beauty and cooler temperatures, September and October are splendid. The Hillside area is renowned for its stunning autumn foliage, with the trees transforming into vibrant reds, oranges, and yellows. This period is great for scenic drives, photography, and enjoying the crisp air on a leisurely walk.

Can I cancel my hotel reservation on Expedia?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Hillside hotel for you.

How much is the nightly rate at a Hillside hotel?

Hotel prices in Hillside often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

10 Best Hotels in Hillside, Milwaukee for 2026

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Our top choices for Hillside hotels

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

1. Aloft by Marriott Milwaukee Downtown

Westown, 1 km from Hillside

Brandon

CA $178 total

includes taxes & fees

Nov 30 - Dec 1

A multi-story hotel with a prominent sign at the top.

2. Drury Plaza Hotel Milwaukee Downtown

Downtown Milwaukee, 1.9 km from Hillside

Maeson

CA $185 total

includes taxes & fees

Dec 3 - Dec 4

A hotel with a modern facade, multiple floors, and a prominent entrance with signage.

3. DoubleTree by Hilton Milwaukee Downtown

Westown, 1.6 km from Hillside

Juan

CA $169 total

includes taxes & fees

Nov 22 - Nov 23

A modern hotel with a prominent "Hyatt Regency" sign, featuring a unique architectural design with a curved section and illuminated pink lighting.

4. Hyatt Regency Milwaukee

Westown, 1.4 km from Hillside

Anna

CA $132 total

includes taxes & fees

Nov 30 - Dec 1

An outdoor seating area with a fire feature, benches with striped cushions, and a modern building in the background.

5. Tru By Hilton Milwaukee Downtown, WI

Downtown Milwaukee, 2.2 km from Hillside

daniel

CA $147 total

includes taxes & fees

Nov 30 - Dec 1

A grand lobby with a marble staircase, a bench, and a decorative wall.

6. Hilton Milwaukee

Westown, 1.6 km from Hillside

Janelle

CA $180 total

includes taxes & fees

Dec 10 - Dec 11

A modern hotel lobby with a reception desk, seating area, and a patterned wall.

7. Holiday Inn Express Milwaukee Downtown by IHG

Downtown Milwaukee, 2.2 km from Hillside

Diane

CA $183 total

includes taxes & fees

Nov 15 - Nov 16

8. The Brewhouse Inn & Suites

Westown, 0.8 km from Hillside

Julie

CA $214 total

includes taxes & fees

Nov 12 - Nov 13

A modern outdoor patio with wicker furniture, a barbecue grill, and a view of a multi-story building.

9. Cambria Hotel Milwaukee Downtown

Westown, 2 km from Hillside

Cindy

CA $161 total

includes taxes & fees

Dec 6 - Dec 7

A modern interior with a central bar area, seating arrangements, and large windows offering natural light.

10. SpringHill Suites by Marriott Milwaukee Downtown

Westown, 1.5 km from Hillside

Tracy Stein

CA $179 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with a large bed, a desk, a chair, and a view of the cityscape.

11. The Marc Hotel

Westown, 1.6 km from Hillside

Timothy

CA $130 total

includes taxes & fees

Dec 2 - Dec 3

A modern lounge area with a fireplace, sofas, and a coffee table.

12. Homewood Suites By Hilton Milwaukee Downtown

Downtown Milwaukee, 2.1 km from Hillside

Chris

CA $168 total

includes taxes & fees

Dec 6 - Dec 7

A grand atrium with multiple levels, ornate columns, and a glass ceiling.

13. Hilton Garden Inn Milwaukee Downtown

Downtown Milwaukee, 2 km from Hillside

Jessica

CA $169 total

includes taxes & fees

Nov 22 - Nov 23

A lobby with a checkered floor, two elevators, and a chandelier.

14. Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

2.2 km from Hillside

Daniel

CA $121 total

includes taxes & fees

Nov 30 - Dec 1

An outdoor seating area with tables, chairs, and a fire feature.

15. Hyatt Place Milwaukee/Downtown

Westown, 0.8 km from Hillside

Margaret

CA $238 total

includes taxes & fees

Nov 23 - Nov 24

A multi-story hotel with a prominent "Courtyard by Marriott" sign, multiple balconies, and a well-lit entrance.

16. Courtyard by Marriott Milwaukee Downtown

Westown, 1.8 km from Hillside

Kyle

CA $183 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with two beds, a desk, a chair, a TV, and a lamp.

17. Ramada by Wyndham Milwaukee

2.3 km from Hillside

Jonny

CA $127 total

includes taxes & fees

Nov 26 - Nov 27

A lobby with a large chandelier, two sofas, a fireplace, and a reception desk.

18. Marriott Milwaukee Downtown

Downtown Milwaukee, 2 km from Hillside

Katie

CA $233 total

includes taxes & fees

Nov 20 - Nov 21

A modern hotel with a prominent entrance, a flag, and a sign indicating the name 'Residence Inn'.

19. Residence Inn Milwaukee Downtown by Marriott

Westown, 1.9 km from Hillside

Bailey

CA $183 total

includes taxes & fees

Nov 22 - Nov 23

A spacious hallway with a polished floor, benches, and chandeliers.

20. The Knickerbocker on the Lake

2 km from Hillside

Sara

CA $152 total

includes taxes & fees

Dec 1 - Dec 2

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Compare popular hotels in Hillside

Property	Star rating	Guest rating
Drury Plaza Hotel Milwaukee Downtown	4.0 star property	9.6 Exceptional 2,451 reviews	View
The Brewhouse Inn & Suites	3.5 star property	9.6 Exceptional 1,205 reviews	View
DoubleTree by Hilton Milwaukee Downtown	4.0 star property	9.2 Wonderful 1,000 reviews	View
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham	4.0 star property	9.0 Wonderful 1,441 reviews	View
Aloft by Marriott Milwaukee Downtown	3.0 star property	8.6 Excellent 1,007 reviews	View

Where to stay in Hillside

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

A cityscape with a river, green spaces, and modern buildings.

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

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A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

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A waterfront cityscape at dusk with a calm river reflecting buildings and a bridge.

Wauwatosa

Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.

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A river with boats, a bridge, and historic buildings along the banks.

Historic Third Ward

Experience a historic warehouse district with a mix of specialty shops, art galleries, and restaurants. Visit the Milwaukee Institute of Art and Design, and enjoy year-round gourmet options at the Milwaukee Public Market, easily accessible via The Hop.

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A modern architectural structure with a unique triangular design, a glass facade, and a cable-stayed bridge.

East Town

East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Cathedral Square. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.

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Top Hillside Hotel Reviews

The Brewhouse Inn & Suites

10/10 Excellent

"Kitchen was good. Pillows could have been better."

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

8/10 Good

"This is an older hotel in an art deco style. There were some quirks but it was unique and interesting! It had a very good restaurant and bar and all the staff were excellent at what they did. The bar had great cocktails and the kitchen was open until 12 and bar until 2 am on Friday & Saturday (10/12 on Sunday). The hotel offered a shuttle service to downtown but it filled up quickly on Friday and Saturday evenings. Strongly recommend making a reservation for those times. We walked downtown a couple of times and it wasn’t a bad walk. We had a really nice stay."

Hotels in Hillside, Milwaukee

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Check prices for these dates

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Guest rating

Our top choices for Hillside hotels

1. Aloft by Marriott Milwaukee Downtown

2. Drury Plaza Hotel Milwaukee Downtown

3. DoubleTree by Hilton Milwaukee Downtown

4. Hyatt Regency Milwaukee

5. Tru By Hilton Milwaukee Downtown, WI

6. Hilton Milwaukee

7. Holiday Inn Express Milwaukee Downtown by IHG

8. The Brewhouse Inn & Suites

9. Cambria Hotel Milwaukee Downtown

10. SpringHill Suites by Marriott Milwaukee Downtown

11. The Marc Hotel

12. Homewood Suites By Hilton Milwaukee Downtown

13. Hilton Garden Inn Milwaukee Downtown

14. Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

15. Hyatt Place Milwaukee/Downtown

16. Courtyard by Marriott Milwaukee Downtown

17. Ramada by Wyndham Milwaukee

18. Marriott Milwaukee Downtown

19. Residence Inn Milwaukee Downtown by Marriott

20. The Knickerbocker on the Lake

Compare popular hotels in Hillside

Where to stay in Hillside

Downtown Milwaukee

West Allis

Wauwatosa

Historic Third Ward

East Town

Top Hillside Hotel Reviews

The Brewhouse Inn & Suites

Frequently asked questions

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