Oconomowoc Vacations from $376

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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!

The Latest Oconomowoc vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Milwaukee-West Medical Center by IHG

Holiday Inn Express Milwaukee-West Medical Center by IHG

2.5 out of 5
Wauwatosa
Price was $512, price is now $376 per person
$376
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
7.8/10 Good! (1,014 reviews)
Room was fine, clean. Area is sketchy AF

Reviewed on Oct 19, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $740, price is now $523 per person
$523
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Spacious room, comfortable bed. Love that when you check in they give you a glass of wine. The bar downstairs is a vibe and stays busy but did not disturb the quietness when I was in my room. Loved the art area in the hotel, I got to meet a local artist. This hotel is located near a lot of restaurants and stores within walkable distance. I parked the rental car and basically walked everywhere.

Reviewed on Oct 24, 2025

The Delafield Hotel

The Delafield Hotel

4 out of 5
Save 100% on your flight
Price was $1,017, price is now $735 per person
$735
per person
Dec 1 - Dec 5
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.6/10 Exceptional! (423 reviews)
A lovely location for a quiet weekend.

Reviewed on Aug 18, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was $631, price is now $469 per person
$469
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.4/10 Exceptional! (1,013 reviews)
The property and rooms are beautiful, especially if you are a beer enthusiast as the building is the former Pabst historic brewhouse. The surrounding area takes advantage of this theme, including breweries within a stone’s throw of the hotel.

Reviewed on Oct 19, 2025

Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Downtown Milwaukee
Price was $652, price is now $486 per person
$486
per person
Jan 15 - Jan 19
found 6 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9.4/10 Exceptional! (915 reviews)
Definitely “overrated”! Expectation shattered! Very expensive! Facility is old and worn and could use updating. Location will be nice very soon following construction. Close to the River Walk which is nice weather permitting.

Reviewed on Oct 21, 2025

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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

Discover the most popular places to visit in Oconomowoc

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 relaxing area.

Fowler Lake Park

Oconomowoc Golf Club

3/5(2 reviews)

Enjoy a round of golf in Oconomowoc at Oconomowoc Golf Club. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Golf Club

Oconomowoc Historical Museum

You can spend time browsing the exhibits at Oconomowoc Historical Museum in Oconomowoc. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Historical Museum

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
$107 nightly
The price is $121 total per night from Oct 26 to Oct 27
$121 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (805 reviews)
Amazing mini kitchen in the room with dishes, toaster and a dishwasher. Free breakfast and a free social hour the nights we stayed with free drinks and food. Amazing experience.

Reviewed on Oct 15, 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
$99 nightly
The price is $112 total per night from Nov 2 to Nov 3
$112 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (645 reviews)
The staff were helpful and friendly. The property looked updated and clean. The parking lot was well lighted. There is new construction in the area. This, it is an upcoming area of Wisconsin.

Reviewed on Oct 11, 2025

Hilton Garden Inn Oconomowoc
TownePlace Suites by Marriott Oconomowoc

TownePlace Suites by Marriott Oconomowoc

3 out of 5
1242 CORPORATE CENTER DRI, Oconomowoc, WI
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $141 total per night from Oct 28 to Oct 29
$141 total
Oct 28 - Oct 29
Total with taxes and fees
9/10 Wonderful! (136 reviews)
Great property

Reviewed on Sep 22, 2025

TownePlace Suites by Marriott Oconomowoc
See all 497 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.

Find the Best Oconomowoc Vacation Packages

Oconomowoc Essential Information

Language
English
Currency
U.S dollars
Population
16,400
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Oconomowoc Historical Museum, Fowler Lake Park and Oconomowoc Golf Club

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Frequently asked questions

How much does an Oconomowoc vacation package cost?
You'll find cheap prices from $376 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?
You can generally find reduced prices and better availability in January, June and September. Take a look at our cheap Oconomowoc vacation packages and you could score some great off-season discounts.
How many days is enough for Oconomowoc?
With around 3 days, you'll have plenty of time to experience popular neighborhoods like Summit Corners and Maplewood during your Oconomowoc vacation. Remember to also add Fowler Lake Park and Oakbrook-Eser Studios and Gallery to your list of must-sees. Looking for more adventures? Consider venturing outside of Oconomowoc on tours and day trips.
Is it worth booking a vacation package to Oconomowoc?
Oconomowoc offers everything you need for a wonderful escape. Get your Oconomowoc vacation off to a flying start by visiting top attractions like Oconomowoc Golf Club.
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.
Does Expedia offer Book Now, Pay Later Oconomowoc vacation packages?
Your Oconomowoc break is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.