Deals on vacations and trips to Oconomowoc

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Oconomowoc flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Save 100% on your flight
Price was $435, price is now $271 per person
$271
per person
Feb 18 - Feb 23
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Save 100% on your flight
Price was $723, price is now $487 per person
$487
per person
Feb 18 - Feb 23
found 21 hours ago
Roundtrip flight included
Orlando (MCO) 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.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $963, price is now $651 per person
$651
per person
Feb 18 - Feb 23
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and a library are also on offer.
Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $630, price is now $428 per person
$428
per person
Feb 18 - Feb 23
found 21 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and valet parking. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $707, price is now $494 per person
$494
per person
Feb 18 - Feb 23
found 21 hours ago
Roundtrip flight included
Orlando (MCO) 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. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Top Oconomowoc hotels deals

Hilton Garden Inn Oconomowoc

Hilton Garden Inn Oconomowoc

3 out of 5
1443 Pabst Farms Cir Oconomowoc WI
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $112 total per night
$112 total
Jan 1 - Jan 2, 2026
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
Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

3 out of 5
1141 Blue Ribbon Drive Oconomowoc WI
Free Cancellation
$103 nightly
The price is $116 total per night
$116 total
Dec 28 - Dec 29
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
TownePlace Suites by Marriott Oconomowoc

TownePlace Suites by Marriott Oconomowoc

3 out of 5
1242 CORPORATE CENTER DRI Oconomowoc WI
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $127 total per night
$127 total
Jan 11 - Jan 12, 2026
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.
Pool
Breakfast included
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
1200 S Moorland Rd Brookfield WI
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $117 total per night
$117 total
Jan 1 - Jan 2, 2026
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 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

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

3 out of 5
1250 S Moorland Rd Brookfield WI
Free Cancellation
$93 nightly
The price is $107 total per night
$107 total
Jan 4 - Jan 5, 2026
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
Renaissance Milwaukee West Hotel

Renaissance Milwaukee West Hotel

4 out of 5
2300 NORTH MAYFAIR RD Milwaukee WI
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $132 total per night
$132 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 5 conference rooms, 24-hour business center, and express check-in. Self parking, a coffee shop, and a communal living room are also offered.
Restaurant
Air conditioning
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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.

Popular places to visit

Lac La Belle

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.

Lac La Belle

Oconomowoc Memorial Hospital

Though Oconomowoc Memorial Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Oconomowoc while you are here.

Oconomowoc Memorial Hospital

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

Frequently asked questions

How much are vacation packages to Oconomowoc?
With vacation packages on offer for only $271, 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.

Photos of local treasures

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