Maplewood Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Maplewood

Price found within the past 48 hours. Click for updated prices.
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
Price was CA $835, price is now CA $734 per person
CA $734
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
8.6/10 Excellent! (818 reviews)
Room was clean, staff was helpful with my child's allergies.

Reviewed on Jun 20, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,619, price is now CA $967 per person
CA $967
per person
Jul 30 - Aug 2
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
Beautiful, historic hotel in downtown Milwaukee. Excellent location, allowing us to walk to various attractions. The staff was always friendly and helpful.

Reviewed on Jun 17, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,130, price is now CA $924 per person
CA $924
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.8/10 Exceptional! (2,655 reviews)
The location of this property was within walking distance of almost everything you woul want to do in Milwuakee. The staff was always helpful and had great suggestions on where to visit ans always helpful with whatever we needed. The coolest hotel we have stayed at with all the art in the galleries and little details in each room and on each floor.

Reviewed on Jun 21, 2026

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was CA $1,020, price is now CA $855 per person
CA $855
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (148 reviews)
Excellent property! Near to everything we wanted to do, and very walkable!! Loved the building! Beautiful!!

Reviewed on Jun 21, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,081, price is now CA $939 per person
CA $939
per person
Sep 11 - Sep 13
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,166 reviews)
We loved the Iron Horse!! Location was fantastic, we walked to several places from the hotel. The room was gorgeous and huge, very comfortable. I agonized over where to stay in milwaukee and really happy with this hotel. The lobby has an oddly strong scent of aftershave that made us laugh. The valet are really friendly, front desk was great too!

Reviewed on Jun 20, 2026

Maplewood Hotel Deals

Okauchee Lake Vacation Rental w/ Boat Dock!

Okauchee Lake Vacation Rental w/ Boat Dock!

Oconomowoc WI
7.8/10 Good! (8 reviews)
"Dirty and not maintained"

Reviewed on Sep 4, 2025

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Okauchee Lake Vacation Rental w/ Boat Dock!
3 Bedroom Okauchee Lake

3 Bedroom Okauchee Lake

Oconomowoc WI
9.6/10 Exceptional! (15 reviews)
Lakeside apartment
"Nice apartment close to our family reunion on a nearby lake. It was above a lively bar but we stayed late at the reunion so were not disturbed by the bar noise. Nice views and well-equipped kitchen. Need to be able to climb a flight of stairs to access the apartment."

Reviewed on Jul 18, 2025

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3 Bedroom Okauchee Lake
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
The price is CA $146 per night from Jul 5 to Jul 6
CA $146
CA $168 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very Good! (904 reviews)
"Very helpful staff check was a breeze"

Reviewed on Jun 21, 2026

Sheraton Milwaukee Brookfield Hotel
See all 241 properties in Maplewood
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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Frequently asked questions

How much does a Maplewood vacation package cost?
Customize your Maplewood package from only CA $734. Choose from any combination of rental cars, flights and hotels to build the getaway of your dreams. Remember to add on a few activities!
How do I get a cheap travel package to Maplewood?
If you love landing a bargain, bundle your bookings into a Maplewood vacation package. Whether you're searching for flights, hotels, rental cars or day tours, you can browse and book them all in one place. You'll have lots of choice at your fingertips too. Expedia has over 550 partner airlines and 1,000,000 hotel options all over the world to pick from. Fly with who you prefer, stay where you like and save a pretty penny — now that's the perfect escape!
Where should I stay in Maplewood?
A vacation in Maplewood isn't complete without visiting Fowler Lake Park, Oconomowoc Memorial Hospital and Oconomowoc Arts Center. Spend your nights close to these popular attractions and make sightseeing simple.
How far in advance should I book my Maplewood vacation?
To score discount prices, book as soon as you can. Airlines generally release flights, along with some of the lowest fares, up to a year in advance. Hotels, car rental and experiences should also be booked early to avoid disappointment. If you've decided on a last-minute getaway in Maplewood, there are always lots of great deals to be had on Expedia. Check them out now!
What does an Expedia Maplewood travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add some experiences and tours. Want to pick your airfare class? That's also easy to do. The choice is all yours when it comes to arranging your ideal Maplewood escape.
What should I know before booking a Maplewood travel package?
Design deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we've got everything you need to plan your getaway. You'll save big dollars just by combining your bookings. Whether you're heading away on a snow and ski adventure or sipping cocktails on a beach, your perfect getaway is only a few clicks away.
Can I choose my airline with a Maplewood Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Maplewood vacation package?
Don't worry if you're rethinking your Maplewood vacation package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We understand your circumstances can change suddenly, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.

Discover the most popular places to visit in Maplewood

The veteran memorial site gives honor and remembrance to all the brave men and women that have fought.

Fowler Lake Park

Explore the great outdoors at Fowler Lake Park, a lovely green space in Oconomowoc. Visit the shops or attend a sporting event in this family-friendly area.

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