Washington Heights Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Washington Heights
Price found within the past 48 hours. Click for updated prices.
Landing Apartments at Mayfair Collection
Wauwatosa
Price was CA $1,314, price is now CA $1,186 per person
CA $1,186
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Beautiful apartment, great lication
Reviewed on Apr 14, 2026
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was CA $1,562, price is now CA $1,312 per person
CA $1,312
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.8/10 Exceptional! (2,655 reviews)
St. Kates is a must stay. No need to leave the property. The food, art and daily live music provide great options for a staycation!
Reviewed on Jun 22, 2026
The Iron Horse Hotel
Fifth Ward
Price was CA $1,653, price is now CA $1,468 per person
CA $1,468
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,162 reviews)
The lobby is beautiful and the staff is super friendly. The room was very clean! The shower glass wall partition into the room could be less transparent. You need to be comfortable showering and using the toilet in view of your spouse or partner… I think an exhibitionist designed it. We didn’t notice the great outdoor seating and bar area until we were waiting for our Uber to leave…. be sure to find it early! The coffee is only 6a.m.-10a.m., and they frequently ran out of either coffee or supplies. However, the coffee was very good! The room phone did not ring to the desk or concierge- just a busy tone, and there wasn’t any cleaning or towel service even though we were there 3 nights. Maybe they could use a door knob hanger to indicate room refreshing needed?
Overall we enjoyed our stay, although we expected more for the price we paid.
Reviewed on Jun 22, 2026
The Brewhouse Inn & Suites
Westown
Price was CA $1,436, price is now CA $1,323 per person
CA $1,323
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (1,071 reviews)
Right by the bucks arena. Room comes with a whole ass kitchen. Its a good time
Reviewed on Jun 22, 2026
Kinn Guesthouse Bay View
Bay View
Price was CA $1,697, price is now CA $1,574 per person
CA $1,574
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (471 reviews)
We stayed in suite #8. It was beautiful and very roomy. It had all the amenities one could need and it was quiet and comfortable despite being right next to the hotel’s restaurant (which was delicious). There are just a few small things that needed tending to and the customer service response to help us with those were very quick. The #3 does not work on the inner keypad to enter the room and our code contained a 3. This has apparently been a problem for a little while. When we called, the gal gave us a new number right away. Also, there was no WiFi passcode in the room or in the communication prior to checkin. We had to call again for that. Service was wonderful again. The lights in the bathroom were partially out and there were no replacement bulbs in the room. We didn’t call about this but were hopeful the housekeepers would resolve the issue for the next guests. We will definitely stay again as these were very minor issues.
Reviewed on Jun 17, 2026
Where to stay in Washington Heights
Find the best Washington Heights areas and neighborhoods for the activities you enjoy most. Learn more about Washington Heights
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.
Washington Heights Hotel Deals
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Jun 29 to Jun 30
CA $223
CA $263 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,556 reviews)
"Room and hotel were very clean. Customer service was terrible. I got double charged and the hotel was less than helpful in resolving the issue."
Reviewed on Jun 22, 2026
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul 7 to Jul 8
CA $251
CA $296 total
Jul 7 - Jul 8
includes taxes & fees
9.6/10 Exceptional! (2,145 reviews)
"Very impressed with the hotel and staff!"
Reviewed on Jun 22, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Jun 28 to Jun 29
CA $150
CA $173 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very good! (911 reviews)
"Hotel was nice but definitely needs some update especially the bathrooms"
Reviewed on Jun 22, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Washington Heights
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.
Milwaukee Art Museum
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
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.
Things to do
Small Group Kayak Tour of Skyline in Milwaukee
CA $115
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
CA $11
per adult
Thrilling Downtown Scavenger Hunt Game in Milwaukee
CA $14
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.