Oconomowoc Vacation Packages

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Your Oconomowoc Vacation

Say goodbye to the hassle of planning and hello to a Oconomowoc vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Halls Park, which is good for nature, watersports and views. If a sightseeing tour is part of the plan during your trip to Oconomowoc, look around top attractions like Fowler Lake Park, Oconomowoc Arts Center and Oconomowoc Golf Club. Stop dreaming and start doing. Check out the broad range of options on Expedia today and finally put your Oconomowoc vacation plans into action!

Top Oconomowoc Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wildwood Lodge

Wildwood Lodge

2.5 out of 5
Price was CA $1,165, price is now CA $1,036 per person
CA $1,036
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
8.8/10 Excellent! (1,016 reviews)
Quiet, clean, large rooms for the price and conveniently located off the interstate. Would stay here again if in the area.

Reviewed on Jul 2, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,596, price is now CA $1,714 per person
CA $1,714
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Staff are very nice

Reviewed on Jul 3, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,597, price is now CA $1,257 per person
CA $1,257
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.8/10 Exceptional! (2,645 reviews)
Great location. The staff was very kind. Cool room

Reviewed on Jul 3, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,741, price is now CA $1,392 per person
CA $1,392
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,176 reviews)
Very clean room. Nice vibe. Would stay again!

Reviewed on Jul 3, 2026

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was CA $1,348, price is now CA $1,150 per person
CA $1,150
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (152 reviews)
Charming place to stay in a lovely location. The bar, Agency, was a delight to have there in the lobby.

Reviewed on Jun 29, 2026

Where to stay in Oconomowoc

Find the best Oconomowoc areas and neighborhoods for the activities you enjoy most. Learn more about Oconomowoc
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Maplewood

Though Maplewood might not have many top sights, you can venture to the surrounding area to see attractions like Oconomowoc Golf Club and Fowler Lake Park.

Find hotels in Maplewood

Ready to book your vacation to Oconomowoc?

 

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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 CA $162 per night from Jul 19 to Jul 20
CA $162
CA $183 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
"Everything good nice people in the office clean room and good breakfast"

Reviewed on Jul 3, 2026

Staybridge Suites Milwaukee West-Oconomowoc by IHG
TownePlace Suites by Marriott Oconomowoc

TownePlace Suites by Marriott Oconomowoc

3 out of 5
1242 CORPORATE CENTER DRI Oconomowoc WI
The price is CA $190 per night from Jul 26 to Jul 27
CA $190
CA $215 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (197 reviews)
"I wish they would have had some bags for businesspeople traveling to take some breakfast to go...not everyone can sit down for breakfast."

Reviewed on Jun 24, 2026

TownePlace Suites by Marriott Oconomowoc
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 CA $185 per night from Jul 26 to Jul 27
CA $185
CA $209 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (693 reviews)
"Consistent. I sty here multiple times throughout the karting season. Pricing is reasonable, property and rooms are clean. Restaurant has lots of options, healthy ones too; very accommodating to food allergies."

Reviewed on Jun 26, 2026

Hilton Garden Inn Oconomowoc
See all 508 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.
All Inclusive Vacations
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Stay near popular Oconomowoc attractions

The entrance to Veterans Memorial Park with stone archways and flags.

Lac La Belle

9.6/10 (14 reviews)
Commune with nature and explore the great outdoors at Lac La Belle during your travels in Oconomowoc. Visit the shops or attend a sporting event in this relaxing area.
See properties

Frequently asked questions

How much does an Oconomowoc vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,036 on Expedia. However, how much your vacation to Oconomowoc costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Oconomowoc?
February, March and April are the best times to search for cheap Oconomowoc vacation packages. Travelling in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Oconomowoc?
Oconomowoc vacations can be as short or long as you like, but to really get a feel for this destination, we'd say 3 days is a good ballpark. This will mean you can fit in major attractions like Oconomowoc Historical Museum and Theatre On Main along with underrated gems. Don't skip neighbourhoods such as Summit Corners and Maplewood either. If you plan wisely, you can even take a day trip outside of Oconomowoc too.
Is it worth booking a vacation package to Oconomowoc?
It's easy to see why an Oconomowoc vacation is on the must-do list of many travellers. Leading attractions like Oconomowoc Arts Centre are just the start of what you can explore here.
How to find the best Oconomowoc package deals?
Begin your search for an Oconomowoc package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Oconomowoc package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oconomowoc escape off to a flying start.
Is it cheaper to book an Oconomowoc vacation as a package?
You can enjoy significant savings on your next Oconomowoc escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oconomowoc?
If you have your Oconomowoc vacation dates confirmed, book as early as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Oconomowoc?

  1. Choose your dates: The things you want to do in Oconomowoc and your preferred season will help you decide when to go.
  2. Plan your budget wisely: On top of the price of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Oconomowoc.
  3. Decide how many days away: Start by making a list of all the activities and sights you want to experience in Oconomowoc. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalized Oconomowoc 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.