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

Next weekend
In two weeks

Our top choices for Oconomowoc holiday rentals

Studio | Free Breakfast. Pool. Gym

Studio | Free Breakfast. Pool. Gym
Oconomowoc
The price is HK$771
HK$1,032 total
includes taxes & fees
28 Dec - 29 Dec
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 HK$766
HK$1,797 total
includes taxes & fees
4 Jan - 5 Jan 2026
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Oconomowoc
10.0 out of 10, Exceptional, (19)
"Clean, cozy and convenient for walks dowtown! Stayed a week- Loved all of the special touches- including lots of towels, keurig pods and the smores basket! Thank you for a liovely stay in Oconomowoc."
United States
sk k.
The price is HK$1,587
HK$3,763 total
includes taxes & fees
25 Dec - 26 Dec
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

Free Breakfast, Gym, Great for Business Travelers!

Free Breakfast, Gym, Great for Business Travelers!
Oconomowoc
The price is HK$921
HK$1,198 total
includes taxes & fees
4 Jan - 5 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 HK$771
HK$1,032 total
includes taxes & fees
28 Dec - 29 Dec
Pool. Gym. Near Aurora Medical Center!

Free Breakfast. Suite Near Aurora Medical Center!

Free Breakfast. Suite Near Aurora Medical Center!
Oconomowoc
The price is HK$1,520
HK$1,933 total
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Suite Near Aurora Medical Center!

Free Breakfast | Great for Business Travelers!

Free Breakfast | Great for Business Travelers!
Oconomowoc
The price is HK$1,520
HK$1,924 total
includes taxes & fees
29 Dec - 30 Dec
Free Breakfast | Great for Business Travelers!

Pool. Gym. Your Next Trip!

Pool. Gym. Your Next Trip!
Oconomowoc
The price is HK$1,520
HK$1,933 total
includes taxes & fees
28 Dec - 29 Dec
Pool. Gym. Your Next Trip!

Free Breakfast, Pool, Hot Tub, Gym. Great Suite!

Free Breakfast, Pool, Hot Tub, Gym. Great Suite!
Oconomowoc
4.0 out of 10, (1)
The price is HK$1,116
HK$1,423 total
includes taxes & fees
22 Dec - 23 Dec
Free Breakfast, Pool, Hot Tub, Gym. Great Suite!

Fast WiFi - Underground Parking - King Bed - Near Froedtert

Fast WiFi - Underground Parking - King Bed - Near Froedtert
Wauwatosa
9.8 out of 10, Exceptional, (22)
"Our stay at Dolphin Square was wonderful. It introduced us to Wawutosa which is a wonderful small with great places to eat - shop - walk 😊"
United States
Mary Ann P.
The price is HK$506
HK$1,890 total
includes taxes & fees
24 Dec - 25 Dec
Fast WiFi - Underground Parking - King Bed - Near Froedtert

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 HK$1,015
HK$2,919 total
includes taxes & fees
3 Jan - 4 Jan 2026
SUNNY! Convenient to Holy Hill, NFL Draft, Harley Reunion, Hiking+Skiing + Golf

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 HK$1,206
HK$2,163 total
includes taxes & fees
5 Jan - 6 Jan 2026
Historic Downtown-Old World Charm-Dining-Coffee

Well Appointed Home Steps from Pewaukee Lake

Well Appointed Home Steps from Pewaukee Lake
Pewaukee
9.8 out of 10, Exceptional, (14)
"Property was awesome and clean. Great spot for stay with family in area."
United States
Brett T.
Well Appointed Home Steps from Pewaukee Lake

Spacious 3-BR with aesthetic living room & fully equipped kitchen in Waukesha

Spacious 3-BR with aesthetic living room & fully equipped kitchen in Waukesha
Waukesha
9.0 out of 10, Wonderful, (2)
"Lovely place. Close to family. Was a good place to stay."
United States
Lee S.
The price is HK$942
HK$2,787 total
includes taxes & fees
23 Dec - 24 Dec
Spacious 3-BR with aesthetic living room & fully equipped kitchen in Waukesha

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, (19)
"Will come and stay again great host and home"
United States
Dion S.
The price is HK$1,050
HK$2,365 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.6 out of 10, Exceptional, (4)
"Clean place. "
United States
John M.
The price is HK$1,424
HK$1,995 total
includes taxes & fees
29 Dec - 30 Dec
Relax & Reboot in this Charming 2-Bedroom Townhome

Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.4 out of 10, Exceptional, (6)
"Needed a low cost option for staying downtown for a business meeting. Super convenient and very nice."
United States
Eric B.
The price is HK$1,362
HK$2,365 total
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Downtown- King Bed-St Johns Acad-Shopping

Comfortable 3 Bedroom with King bed in Waukesha

Comfortable 3 Bedroom with King bed in Waukesha
2.0 star property
Waukesha
The price is HK$1,404
HK$3,749 total
includes taxes & fees
19 Jan - 20 Jan 2026
Comfortable 3 Bedroom with King bed in Waukesha

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 HK$482
HK$1,861 total
includes taxes & fees
22 Dec - 23 Dec
King Bed - FAST WIFI ~ Near Froedtert ~ Undergrnd Parking

King Bed-FAST WiFi - Undrgrd Parking - Near Froedtert

King Bed-FAST WiFi - Undrgrd Parking - Near Froedtert
Wauwatosa
10.0 out of 10, Exceptional, (13)
"Great location and Ian was very responsive to any/all questions."
United States
Tyler B.
The price is HK$482
HK$1,897 total
includes taxes & fees
6 Jan - 7 Jan 2026
King Bed-FAST WiFi - Undrgrd Parking - Near Froedtert
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

Search for holiday rentals in Oconomowoc on Expedia! You can easily find your home rentals, villas, holiday apartments in Oconomowoc using one of the methods below:

  • View our selection of featured holiday rentals in Oconomowoc
  • Use the map to find apartments and other holiday homes in the Oconomowoc neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oconomowoc while they last

Look no further and take a look at our great range of rental properties in Oconomowoc!

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. Other favourite homes for rent in Oconomowoc are Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom! and Beautiful Historic Tudor Mansion with sandy Private Beach.

How many holiday rentals are there in Oconomowoc?

With 21 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 Oconomowoc Historical Museum and Oconomowoc Arts Center. Other places in town to visit include Oconomowoc Golf Club and Oakbrook-Eser Studios and Gallery.

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.