Port Washington Vacation Packages

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Your Port Washington Vacation

Our vacation packages to Port Washington provide endless opportunities to indulge in new sights, sounds and activities. And with all the planning worked out, you can kick back and enjoy your city break without a worry in the world. Want to explore your surroundings? 1860 Light Station and Museum, The Chocolate Chisel and Possibility Playground are three of the best places to visit during a trip to Port Washington. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Port Washington vacation is a walk in the park with Expedia.

Top Port Washington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Marquette
Price was CA $1,402, price is now CA $1,249 per person
CA $1,249
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9/10 Wonderful! (1,342 reviews)
Nice retro style hotel. Would stay again

Reviewed on Jul 4, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,915, price is now CA $1,534 per person
CA $1,534
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.8/10 Exceptional! (2,645 reviews)
Checkin was great. Free champagne! Gave us transportation guidance.

Reviewed on Jul 5, 2026

Landing Apartments at Mayfair Collection

Landing Apartments at Mayfair Collection

4 out of 5
Wauwatosa
Price was CA $1,683, price is now CA $1,448 per person
CA $1,448
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!

Reviewed on May 21, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $2,009, price is now CA $1,766 per person
CA $1,766
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,176 reviews)
Beautiful property! I like the outdoor bar and restaurant on site. Rooms are very nice and very clean!. Comfortable beds.

Reviewed on Jul 4, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,651, price is now CA $1,486 per person
CA $1,486
per person
Aug 20 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,555 reviews)
Room very neat but not dusted everything else was good

Reviewed on Jul 4, 2026

Ready to book your vacation to Port Washington?

 

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Port Washington Hotel Deals

The Harborview on Lake Michigan, an Ascend Collection Hotel

The Harborview on Lake Michigan, an Ascend Collection Hotel

3 out of 5
135 E Grand Ave Port Washington WI
Fully refundable
The price is CA $224 per night from Jul 19 to Jul 20
CA $224
CA $291 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (619 reviews)
"Great place to stay in a beautiful town."

Reviewed on Jul 1, 2026

The Harborview on Lake Michigan, an Ascend Collection Hotel
Holiday Inn Express & Suites Port Washington by IHG

Holiday Inn Express & Suites Port Washington by IHG

2.5 out of 5
350 E Seven Hills Rd Port Washington WI
Fully refundable
The price is CA $240 per night from Jul 12 to Jul 13
CA $240
CA $294 total
Jul 12 - Jul 13
includes taxes & fees
9/10 Wonderful! (87 reviews)
"There was some construction in front of the hotel we were not made aware of and the pool had closed down early one night. Those were the only two negatives, the breakfast, the staff, the location, and the rooms are beautiful."

Reviewed on Jul 1, 2026

Holiday Inn Express & Suites Port Washington by IHG
The Port Hotel

The Port Hotel

2 out of 5
101 E Main St Port Washington WI
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from Jul 9 to Jul 10
CA $233
CA $264 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (173 reviews)
"The hotel is old but updated and our room was perfect. I met with Jim and he was very informative! We will come back and spend more time Thanks! Jim Ferguson"

Reviewed on Jul 2, 2026

The Port Hotel
See all 350 properties in Port Washington
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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Stay near popular Port Washington attractions

Possibility Playground

8.6/10 (8 reviews)
Enjoy an outing to Possibility Playground during your stay in Port Washington. Stroll along the waterfront or experience the area's festivals.
See properties

Frequently asked questions

How much does a Port Washington vacation package cost?
Offering great value package deals from CA $1,249 on Expedia, you'll be pleasantly surprised at how much a vacation to Port Washington costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Port Washington?
If you're hoping to snag a cheap Port Washington vacation package, consider visiting in January, February and November. You'll generally find lower rates on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Port Washington?
With a well-planned itinerary, you can easily visit the main Port Washington attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Port Washington vacation for longer.
Is it worth booking a vacation package to Port Washington?
Boasting a host of highlights starting with its amazing history, Port Washington is a good vacation destination. Whether you want to visit attractions like The Chocolate Chisel and Possibility Playground or take the path less travelled, you'll have loads to see and do on your Port Washington vacation.
How to find the best Port Washington package deals?
Use Expedia's filter tool to find some fabulous Port Washington package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Port Washington package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Port Washington vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Port Washington trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Port Washington?
If you have your Port Washington vacation dates confirmed, book early to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Port Washington?

  1. Pick your dates: The things you'd like to do in Port Washington and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Port Washington.
  3. Determine how many days away: Start by listing all the sights and activities you'd like to get to in Port Washington. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Port Washington vacation package.

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