Oconomowoc Vacations from ￥238,330

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The Latest Oconomowoc Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Milwaukee Downtown

Hampton Inn & Suites Milwaukee Downtown

2.5 out of 5
Westown
per person
Oct 23 - Oct 27
found 5 hours ago
Roundtrip flight included
Fukuoka (FUK) to Milwaukee (MKE)
6.6/10 (1,007 reviews)
For the triathlon race the location was great less than a mile away.

Reviewed on Aug 12, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Milwaukee (MKE)
9.2/10 Wonderful! (1,015 reviews)
Easily the nicest hotel I’ve ever stayed at, fantastic service. I will be back!

Reviewed on Aug 13, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
It met our requirements for this trip.

Reviewed on Aug 12, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Milwaukee (MKE)
9.8/10 Exceptional! (2,392 reviews)
Stayed with my daughter for a show at the theatre across the street. Staff was lovely and helpful. Excellent location. Very nice hotel. Loved the art.

Reviewed on Aug 11, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Fukuoka (FUK) to Milwaukee (MKE)
9.6/10 Exceptional! (1,683 reviews)
Amazing hotel in the BEST location. Gorgeous!!

Reviewed on Aug 13, 2025

Find the Best Oconomowoc Vacation Packages

Oconomowoc Hotel Deals

Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

3 out of 5
1141 Blue Ribbon Drive, Oconomowoc, WI
Fully refundable
The price is ￥16,345 per night from Sep 1 to Sep 2
￥16,345
￥18,470 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (779 reviews)
"Very comfortable place to stay."

Reviewed on Aug 11, 2025

Staybridge Suites Milwaukee West-Oconomowoc by IHG
Hilton Garden Inn Oconomowoc

Hilton Garden Inn Oconomowoc

3 out of 5
1443 Pabst Farms Cir, Oconomowoc, WI
Fully refundableReserve now, pay when you stay
The price is ￥18,718 per night from Sep 1 to Sep 2
￥18,718
￥21,152 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (635 reviews)
"Clean and modern! Bed is very comfy!"

Reviewed on Aug 10, 2025

Hilton Garden Inn Oconomowoc
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc
10/10 Exceptional! (1 review)
"Katie was the most welcoming host you can ask for. She was really sweet and the home was just breathtaking. Lots of space, big kitchen, and plenty of activities to pass time with. We were a group of 10 adult men celebrating for a bachelor party and we did not regret the house we selected. The lake ..."

Reviewed on Aug 6, 2025

Get rates
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle
See all 507 properties in Oconomowoc
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

How much does an Oconomowoc vacation package cost?
You'll find cheap prices from ￥238,330 on Expedia for your Oconomowoc escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oconomowoc costs.
What are the cheapest months to go to Oconomowoc?
February, March and April are great times to look for cheap Oconomowoc vacation packages. Traveling in quieter periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Oconomowoc?
To get the most out of your Oconomowoc vacation, we suggest staying for 3 days. Divide your time between visiting Lac La Belle, Fowler Lake Park and other well-known attractions, in addition to exploring neighborhoods like Summit Corners and Maplewood. If you've got some spare time, add a day trip to your Oconomowoc vacation itinerary.
Is it worth booking a vacation package to Oconomowoc?
Oconomowoc is a good vacation destination with attractions like Oconomowoc Arts Center among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, an Oconomowoc vacation promises a good time for everyone.
How to find the best Oconomowoc package deals?
Bagging a cheap Oconomowoc package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Oconomowoc package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book an Oconomowoc vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Oconomowoc vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Oconomowoc?
If you've got your Oconomowoc travel dates confirmed, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to Oconomowoc?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite season and the type of activities on offer will also help you decide when to escape to Oconomowoc.
  2. Set your budget: Factor in expenses such as flights, transportation and food when calculating how much to save for your trip to Oconomowoc. Then, select a hotel that fits your budget, whether that's an affordable stay or a lavish getaway.
  3. Decide how long to go away for: Now that you're more familiar with Oconomowoc, you can work out the right length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Oconomowoc vacation package.

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