Oconomowoc Vacation Packages 2026 from $435

Oconomowoc flight + hotel vacation packages

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

Sheraton Milwaukee Brookfield Hotel

$435

per person

Aug 19 - Aug 22

found 6 hours ago

Roundtrip flight included

New York (JFK) to Milwaukee (MKE)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$639

per person

Aug 19 - Aug 22

found 6 hours ago

Roundtrip flight included

New York (JFK) to Milwaukee (MKE)

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

The Iron Horse Hotel

Fifth Ward

$571

per person

Aug 19 - Aug 22

found 6 hours ago

Roundtrip flight included

New York (JFK) to Milwaukee (MKE)

This boutique hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. WiFi in public areas is free.

Kinn Guesthouse Downtown

Downtown Milwaukee

$586

per person

Aug 19 - Aug 22

found 6 hours ago

Roundtrip flight included

New York (JFK) to Milwaukee (MKE)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Self parking and express check-out are also offered on site.

Kinn Guesthouse Bay View

Bay View

$565

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

New York (NYC) to Milwaukee (MKE)

A restaurant and a bar/lounge are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a lobby fireplace are also offered.

Top Oconomowoc hotels deals

Staybridge Suites Milwaukee West-Oconomowoc by IHG

1141 Blue Ribbon Drive Oconomowoc WI

Free Cancellation

$103 nightly

$116 total

Aug 17 - Aug 18

Total with taxes and fees

This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a terrace, and a picnic area are also on offer.

TownePlace Suites by Marriott Oconomowoc

1242 CORPORATE CENTER DRI Oconomowoc WI

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$151 total

Aug 16 - Aug 17

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a garden, and a picnic area are also on offer.

Hilton Garden Inn Oconomowoc

1443 Pabst Farms Cir Oconomowoc WI

$122 nightly

$138 total

Aug 9 - Aug 10

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

Jul 26 - Jul 27

Total with taxes and fees

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$98 total

Jul 21 - Jul 22

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

The Ingleside Hotel

2810 Golf Road Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Jul 23 - Jul 24

Total with taxes and fees

A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.

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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.

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 are vacation packages to Oconomowoc?

With vacation packages on offer for only $435, you won't need to max out the credit card for your trip to Oconomowoc. Travelocity can help. Combine hotels, flights and tours into a package and land impressive discounts. The more you book, the more you save.

How long should my Oconomowoc vacation be?

Around 2 nights is the average amount of time travelers spend in Oconomowoc. But the perfect trip length comes down to how many cherished memories you want to make. Why not stay a little longer and uncover some hidden gems?

Where can I get the best vacation package deals for Oconomowoc?

There are fantastic Oconomowoc package deals to be gained with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties around the globe? Keep this in mind when you're ready to check another destination off your bucket list.

Why should I book my Oconomowoc vacation package with Travelocity?

By booking your hotel, flights, car rental and activities altogether, you'll save both time and money. We offer an expert team of customer service specialists available 24/7, and you'll know that you're always getting the best deal in town with our Price Match Guarantee. So, what's stopping you? Book that dream vacation today and get packing!

Can I save on my Oconomowoc car rental if I bundle it with my hotel or flight?

You certainly can — combine your car, flight and hotel into an Oconomowoc vacation package and you'll save a ton. With so many places to explore in Oconomowoc, that set of wheels will more than come in handy. Once you're behind the wheel, get out on the wide open road and head toward Wrigley Field, a must-see attraction roughly 90 mi from Oconomowoc.

Which airport is best for Oconomowoc?

Oconomowoc has two airports to select from — General Mitchell Intl. Airport (MKE) (30 mi away from the city center) and Dane County Regional Airport (MSN) (45 mi away from central Oconomowoc).

What is there to do in Oconomowoc?

While veering off the tourist trail is rewarding, you really shouldn't miss the popular sights that make a destination famous. Oconomowoc Arts Center and Oakbrook-Eser Studios and Gallery are a couple of them in Oconomowoc.

Where should I stay when visiting Oconomowoc?

The Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel is the first choice of many visitors. Book as soon as possible to avoid missing out.