Hillside Vacations from $359

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The Latest Hillside Vacation Packages

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

Wildwood Lodge

2.5 out of 5
per person
Sep 23 - Sep 26
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
8.4/10 Very Good! (1,025 reviews)
We were there with baseball group and everyone was very accommodating

Reviewed on Aug 11, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (402 reviews)
The beds are so comfortable and the decor is great! There is really no staff there to connect with, which is different. You go and leave like its an apartment- they just send codes and there is no service desk. I loved the place! Very steep stairs for older people to go up.

Reviewed on Aug 10, 2025

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
Downtown Sheboygan
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
8.6/10 Excellent! (953 reviews)
It was a nice room with a kitchenette

Reviewed on Aug 9, 2025

My Place Hotel - Mount Pleasant

My Place Hotel - Mount Pleasant

3 out of 5
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
8.8/10 Excellent! (407 reviews)
I didn’t realize until after I booked the room that there was no free continental breakfast, which was a little bit of a bummer, but the room was really nice and clean

Reviewed on May 25, 2025

The Plaza Hotel

The Plaza Hotel

3 out of 5
Downtown Milwaukee
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
8.8/10 Excellent! (1,113 reviews)
Excellent location.

Reviewed on Aug 9, 2025

Where to stay in Hillside

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

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.

Find hotels in Downtown Milwaukee

Hillside Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
$205 nightly
The price is $242 total per night from Sep 1 to Sep 2
$242 total
Sep 1 - Sep 2
Total includes taxes and fees
9.4/10 Exceptional! (1,686 reviews)
"Excellent option for couples"

Reviewed on Aug 10, 2025

The Pfister Hotel
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $183 total per night from Aug 13 to Aug 14
$183 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (1,339 reviews)
"Beautiful rooms"

Reviewed on Aug 11, 2025

Potawatomi Hotel & Casino
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Aug 31 to Sep 1
$100 total
Aug 31 - Sep 1
Total includes taxes and fees
8.2/10 Very Good! (380 reviews)
"Properyu was clean. Beds were hard"

Reviewed on Aug 10, 2025

Sheraton Milwaukee Brookfield Hotel
See all 1,228 properties in Hillside
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Hillside

Harley-Davidson Museum showing interior views

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 County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo
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

Things to do

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

$9
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

$26
per adult
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
Kayaks Rentals Everyday

Milwaukee Kayak Rental

$55
per adult
Milwaukee Kayak Rental
See all activities in Milwaukee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.