Oconomowoc Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Oconomowoc holiday rentals

Studio | Free Breakfast. Pool. Gym

Studio | Free Breakfast. Pool. Gym
Oconomowoc
The price is NZ$226
includes taxes & fees
12 Jan - 13 Jan 2026
Studio | Free Breakfast. Pool. Gym

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
2.0 star property
Oconomowoc
The price is NZ$398
includes taxes & fees
12 Jan - 13 Jan 2026
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Free Breakfast, Gym, Great for Business Travelers!

Free Breakfast, Gym, Great for Business Travelers!
Oconomowoc
The price is NZ$263
includes taxes & fees
12 Jan - 13 Jan 2026
Free Breakfast, Gym, Great for Business Travelers!

Pool. Gym. Near Aurora Medical Center!

Pool. Gym. Near Aurora Medical Center!
Oconomowoc
The price is NZ$226
includes taxes & fees
12 Jan - 13 Jan 2026
Pool. Gym. Near Aurora Medical Center!

Free Breakfast | Great for Business Travelers!

Free Breakfast | Great for Business Travelers!
Oconomowoc
The price is NZ$422
includes taxes & fees
12 Jan - 13 Jan 2026
Free Breakfast | Great for Business Travelers!

Free Breakfast. Suite Near Aurora Medical Center!

Free Breakfast. Suite Near Aurora Medical Center!
Oconomowoc
The price is NZ$422
includes taxes & fees
12 Jan - 13 Jan 2026
Free Breakfast. Suite Near Aurora Medical Center!

Pool. Gym. Your Next Trip!

Pool. Gym. Your Next Trip!
Oconomowoc
The price is NZ$422
includes taxes & fees
12 Jan - 13 Jan 2026
Pool. Gym. Your Next Trip!

King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking
Wauwatosa
10.0 out of 10, Exceptional, (4)
"Came to the Milwaukee area for a family function and Ian’s place was perfect. Convenient to everything you need and underground parking was a nice perk. Would check his place out for any return trips."
United States
Jane H.
The price is NZ$422
includes taxes & fees
6 Jan - 7 Jan 2026
King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf
Hartford
10.0 out of 10, Exceptional, (4)
"Gorgeous interior, responsive host, clear instructions. Enjoyed proximity to hiking, cafe, and arcade. "
United States
M. M.
The price is NZ$637
includes taxes & fees
2 Jan - 3 Jan 2026
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

Live in Chic and Comfort: Experience Our Thoughtfully Designed 1 Bed with Loft!

Live in Chic and Comfort: Experience Our Thoughtfully Designed 1 Bed with Loft!
Germantown
9.0 out of 10, Wonderful, (4)
"Such a sweet, cozy little place with all the amenities of a large space. We loved the area it was super quiet and lots within walking distance. The neighbors were also very nice!"
United States
Debbie M.
The price is NZ$549
includes taxes & fees
1 Jan - 2 Jan 2026
Live in Chic and Comfort: Experience Our Thoughtfully Designed 1 Bed with Loft!

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
Waukesha
9.8 out of 10, Exceptional, (20)
"Beautiful home, modern amenities, easy location for food and shopping"
United States
Emily G.
The price is NZ$523
includes taxes & fees
6 Jan - 7 Jan 2026
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.4 out of 10, Exceptional, (6)
"We were in town for a wedding and this place was perfect. Great location, close to restaurants, shopping and the wedding venue was only 15 minutes away. Unit was very clean and comfortable. It had everything we needed. We loved Angelina's Restaurant which is right around the corner. If you stay here definitely eat at Angelina's."
United States
Christopher M.
The price is NZ$396
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Downtown Luxury-Lake-Coffee-Spa like BA

Comfortable 3 Bedroom with King bed in Waukesha

Comfortable 3 Bedroom with King bed in Waukesha
2.0 star property
Waukesha
The price is NZ$654
includes taxes & fees
6 Jan - 7 Jan 2026
Comfortable 3 Bedroom with King bed in Waukesha

Pet-Friendly Farmhouse 2 Bedroom Near UWW Campus, Starin Park, & Kettle Moraine!

Pet-Friendly Farmhouse 2 Bedroom Near UWW Campus, Starin Park, & Kettle Moraine!
Whitewater
9.8 out of 10, Exceptional, (17)
"Was perfect for our weekend visit. Location was great for UW Whitewater parents weekend. Would definitely stay again!!"
United States
Chad A.
The price is NZ$339
includes taxes & fees
26 Jan - 27 Jan 2026
Pet-Friendly Farmhouse 2 Bedroom Near UWW Campus, Starin Park, & Kettle Moraine!

Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.6 out of 10, Exceptional, (7)
"Needed a low cost option for staying downtown for a business meeting. Super convenient and very nice."
United States
Eric B.
The price is NZ$523
includes taxes & fees
1 Jan - 2 Jan 2026
Historic Downtown- King Bed-St Johns Acad-Shopping

Brew City Game Room Fenced Yard Sleeps 13

Brew City Game Room Fenced Yard Sleeps 13
2.0 star property
Wauwatosa
10.0 out of 10, Exceptional, (1)
"Amazing location off the highway was able to make it into the city efficiently. Would recommend!"
United States
Dario
The price is NZ$910
includes taxes & fees
20 Jan - 21 Jan 2026
Brew City Game Room Fenced Yard Sleeps 13

King Bed - Near Froedtert - Fast WiFi - Underground Parking

King Bed - Near Froedtert - Fast WiFi - Underground Parking
Wauwatosa
9.2 out of 10, Wonderful, (23)
"Great place. Great location for me. If you're visit is around Hwy 100, in West Allis or Wauwatosa this is your place."
United States
Robert D.
The price is NZ$422
includes taxes & fees
5 Jan - 6 Jan 2026
King Bed - Near Froedtert - Fast WiFi - Underground Parking

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin
8.6 out of 10, Excellent, (9)
"Awesome place!"
United States
Daniel M.
The price is NZ$4,643
includes taxes & fees
12 Jan - 13 Jan 2026
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars
Hartford
10.0 out of 10, Exceptional, (5)
"This is a nice place to stay. The bedrooms are all spacious, clean and very comfy. The communication with the host was great. I would stay here again. "
United States
Nicole D.
The price is NZ$1,523
includes taxes & fees
5 Jan - 6 Jan 2026
Luxury 5BR 3.5B sleeps 17 w/ Hot Tub, Home Theater near Skiing, Golf, & Bars

Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (5)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is NZ$479
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Downtown-Old World Charm-Dining-Coffee
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oconomowoc Hotel Reviews

Find out more about Oconomowoc

Everything you need to know about Oconomowoc holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oconomowoc holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oconomowoc holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oconomowoc holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oconomowoc. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oconomowoc holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oconomowoc holiday rentals we have selected for you start as low as NZ$355 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oconomowoc rentals

At Expedia, we put the best Oconomowoc holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oconomowoc rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oconomowoc holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oconomowoc. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oconomowoc?

Yes, there are holiday rentals in Oconomowoc close to Fowler Lake Park, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Oconomowoc. Make sure you have time to check out the cafés and sporting events during your trip.

What are some of the best holiday rentals that Oconomowoc has to offer?

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle: This highly rated holiday home rental in Oconomowoc is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. Another good choice for your trip to Oconomowoc is Beautiful Historic Tudor Mansion with sandy Private Beach.

How many holiday rentals are there in Oconomowoc?

With 22 Expedia holiday rentals, you're guaranteed to find just the right place for your Oconomowoc stay.

What’s there to see and do in Oconomowoc?

Enjoy the outdoors at Fowler Lake Park and Lac La Belle, or simply take in cultural attractions like Theatre On Main and Oconomowoc Historical Museum. Other places in town to visit include Oconomowoc Arts Center and Oconomowoc Golf Club.

What’s a holiday rental in Oconomowoc like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oconomowoc. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.