Washington Heights Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, 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.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,444, price is now CA $1,122 per person
CA $1,122
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (456 reviews)
The room was very spacious and clean. We loved the convenience of the area and the many amenities es provided on site. The team did an amazing job of communicating with rapid speed.

Reviewed on Mar 23, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $3,564, price is now CA $2,347 per person
CA $2,347
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (2,047 reviews)
Excellent hotel in every aspect.

Reviewed on Apr 11, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,643, price is now CA $1,307 per person
CA $1,307
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (1,417 reviews)
Clean room, nice casino

Reviewed on Apr 3, 2026

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Price was CA $1,856, price is now CA $1,481 per person
CA $1,481
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Honestly 5+ stars to the women running this place. They’re doing their jobs and doing it with kindness, friendliness and above all helpful and professional. Give them a raise!! It was spotless and comfortable. Good reason why their ratings are above other hotels in the area charging twice as much for the name.

Reviewed on Mar 26, 2026

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was CA $2,080, price is now CA $1,670 per person
CA $1,670
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (1,047 reviews)
Very cool building. Check in was fast and easy! The room was beautiful.

Reviewed on Apr 3, 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 skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

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

Washington Heights Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $306 per night from Apr 19 to Apr 20
CA $306
CA $360 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (2,061 reviews)
Excellent hotel in every aspect.

Reviewed on Apr 11, 2026

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
The price is CA $193 per night from Apr 13 to Apr 14
CA $193
CA $228 total
Apr 13 - Apr 14
includes taxes & fees
9.2/10 Wonderful! (1,429 reviews)
Worth it!!!

Reviewed on Apr 10, 2026

Potawatomi Hotel & Casino
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
The price is CA $249 per night from Apr 19 to Apr 20
CA $249
CA $294 total
Apr 19 - Apr 20
includes taxes & fees
9.8/10 Exceptional! (2,622 reviews)
Gorgeous hotel and amazing staff!

Reviewed on Apr 9, 2026

Saint Kate - The Arts Hotel
See all 1,168 properties in Washington Heights
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
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Frequently asked questions

How much does a Washington Heights vacation package cost?
Discover the best of Washington Heights from as little as CA $1,122. We offer a great selection of rental cars, hotels and flights to suit your travel style. Score even more discounts when you add a couple of sightseeing tours to your package.
How do I get a cheap travel package to Washington Heights?
If you love bargains, combine your bookings into a Washington Heights vacation package. Whether you're searching for flights, hotels, rental cars or tours, you can book them all in one place. You'll have a wealth of choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 properties throughout the world to take your pick of. Fly with who you want, find a room where you like and save a tidy sum — now that's the ideal vacation!
Where should I stay in Washington Heights?
Urban explorers come from all over the world to see Milwaukee Art Museum and American Family Field in Washington Heights. Book yourself a room within a stone's throw of these awesome attractions and visit them whenever you please.
What are the top hotels in Washington Heights?
Upscale Milwaukee Duplex is one of Washington Heights's most well-known hotels. Lock in a room here and you'll sleep soundly knowing you're in good hands.
How far in advance should I book my Washington Heights vacation?
Smart travelers will likely want to book early. You can normally compare international airfares on Expedia up to 12 months before your intended flight. If you're booking at the last minute, fear not. Low prices occasionally occur just weeks prior to departure.
What does an Expedia Washington Heights travel package include?
Flights, hotels and a reliable car for all your fun road trip adventures. Simply pick and choose your favorite bundle and get access to incredible deals. Once you've made your booking, add on a couple of activities and tours and watch your savings grow. When it comes to planning your Washington Heights getaway, the choice is all yours!
What should I know before booking a Washington Heights travel package?
Bundling your bookings into a Washington Heights vacation package is the easiest way to organize your trip. Not only that, you'll get great discounts when you combine your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Washington Heights Expedia vacation package?
You certainly can. Expedia has access to more than 550 partner airlines all over the world, so select the carrier that suits your needs.
If I'm not able to travel, can I cancel my Washington Heights vacation package?
We totally get it — unexpected stuff happens. If you've booked a Washington Heights vacation package and have to amend or cancel it, we're here to help. It's always worth visiting our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a fee.

Discover the most popular places to visit in Washington Heights

Harley-Davidson Museum

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 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

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.

Potawatomi Bingo Casino
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.