Oconomowoc Vacation Packages 2026 from $785

Oconomowoc flight + hotel vacation packages

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

Hyatt Regency Milwaukee

Westown

$785

per person

Nov 5 - Nov 8

found 18 hours ago

Roundtrip non-stop flight included

Richmond (RIC) to Milwaukee (MKE)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a snack bar/deli are also offered.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$1,202

per person

Nov 5 - Nov 8

found 18 hours ago

Roundtrip non-stop flight included

Richmond (RIC) 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 Westin Milwaukee

Downtown Milwaukee

$798

per person

Nov 5 - Nov 8

found 18 hours ago

Roundtrip non-stop flight included

Richmond (RIC) to Milwaukee (MKE)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a computer station, and dry cleaning are also on offer.

Saint Kate - The Arts Hotel

Downtown Milwaukee

$959

per person

Nov 13 - Nov 15

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Milwaukee (MKE)

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

Kinn Guesthouse Bay View

Bay View

$864

per person

Nov 5 - Nov 8

found 18 hours ago

Roundtrip non-stop flight included

Richmond (RIC) 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

$105 nightly

$119 total

Oct 4 - Oct 5

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.

Pool

Breakfast included

Hilton Garden Inn Oconomowoc

1443 Pabst Farms Cir Oconomowoc WI

$114 nightly

$129 total

Oct 11 - Oct 12

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.

Pool

Hot Tub

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$90 total

Oct 4 - Oct 5

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. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$87 total

Oct 4 - Oct 5

Total with taxes and fees

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.

Pool

Pet friendly

Studio 6 Extended Stay Milwaukee Brookfield WI

325 N Brookfield Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$88 total

Oct 1 - Oct 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A safe deposit box and laundry facilities are also provided.

Pet friendly

Parking included

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

1250 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$113 total

Oct 30 - Oct 31

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, 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. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

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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 $785, 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.