A boat on a calm lake with a forested shoreline in the background.

Oconomowoc Holiday Rentals

  • 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

In two weeks
In two months
In three months
In four months

Our top choices for Oconomowoc holiday rentals

1. Charming Historic Upper Walk to Downtown & Lakes

Charming Historic Upper Walk to Downtown & Lakes
Oconomowoc
10.0 out of 10, Exceptional, (42 reviews)
"Beautiful, comfortable house within easy walking distance of downtown and the beach. Thoughtful hosts with great communication. Thanks for a great return stay!"
United States
Mark G.
The price is HK$1,670
HK$4,201 total
includes taxes & fees
27 Sept - 28 Sept
Charming Historic Upper Walk to Downtown & Lakes

2. Private Hot Tub • Bright Home Near Downtown

Private Hot Tub • Bright Home Near Downtown
Oconomowoc
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was wonderful. Our host was very responsive to questions, and the home was welcoming and had all needed amenities. "
United States
Heather F.
The price is HK$1,401
HK$2,656 total
includes taxes & fees
29 Sept - 30 Sept
Private Hot Tub • Bright Home Near Downtown

3. Spacious Accessible Studio w/ Walk-In Shower

Spacious Accessible Studio w/ Walk-In Shower
Oconomowoc
The price is HK$808
HK$1,090 total
includes taxes & fees
4 Oct - 5 Oct
Spacious Accessible Studio w/ Walk-In Shower

4. Sytlish Retreat Near Wedding Venues & Downtown

Sytlish Retreat Near Wedding Venues & Downtown
Oconomowoc
10.0 out of 10, Exceptional, (28 reviews)
"Incredible stay in such a beautiful home! "
United States
Saarah B.
The price is HK$1,813
HK$4,353 total
includes taxes & fees
24 Sept - 25 Sept
Sytlish Retreat Near Wedding Venues & Downtown

5. Waterfront Lake Cottage - Upper Nemahbin Lake

Waterfront Lake Cottage - Upper Nemahbin Lake
Peninsular Park
9.6 out of 10, Exceptional, (38 reviews)
"The entire process of renting this house was easy and streamlined. The hosts and the property itself were top notch. Highly recommend!"
United States
Payton C.
The price is HK$1,863
HK$5,532 total
includes taxes & fees
28 Sept - 29 Sept
Waterfront Lake Cottage - Upper Nemahbin Lake

6. Queen Studio Suite w/ Kitchenette in Oconomowoc

Queen Studio Suite w/ Kitchenette in Oconomowoc
Oconomowoc
The price is HK$808
HK$1,090 total
includes taxes & fees
4 Oct - 5 Oct
Queen Studio Suite w/ Kitchenette in Oconomowoc

7. Accessible 1BR Suite | Pool & Daily Breakfast

Accessible 1BR Suite | Pool & Daily Breakfast
Oconomowoc
The price is HK$965
HK$1,267 total
includes taxes & fees
18 Oct - 19 Oct
Accessible 1BR Suite | Pool & Daily Breakfast

8. Accessible 1-BR Queen Suite w/ Roll-In Shower

Accessible 1-BR Queen Suite w/ Roll-In Shower
Oconomowoc
The price is HK$965
HK$1,267 total
includes taxes & fees
4 Oct - 5 Oct
Accessible 1-BR Queen Suite w/ Roll-In Shower

9. Accessible 1-BR Suite w/ Two Double Beds

Accessible 1-BR Suite w/ Two Double Beds
Oconomowoc
The price is HK$965
HK$1,267 total
includes taxes & fees
4 Oct - 5 Oct
Accessible 1-BR Suite w/ Two Double Beds

10. 2-BR Suite w/ King & Double Beds + Kitchen

2-BR Suite w/ King & Double Beds + Kitchen
Oconomowoc
10.0 out of 10, Exceptional, (1 review)
"The two bedroom suite was perfect! The room was spotless and the furnishings were comfortable. They had breakfast and a social hour in the evening. It was very nice. We didn’t use the pool and it was great. Would definitely stay here again."
United States
Sharon J.
The price is HK$1,600
HK$2,065 total
includes taxes & fees
4 Oct - 5 Oct
2-BR Suite w/ King & Double Beds + Kitchen

11. Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast
Oconomowoc
"."
United States
Rhonda M.
The price is HK$1,600
HK$2,065 total
includes taxes & fees
4 Oct - 5 Oct
Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

12. Accessible 2-BR Suite w/ Tub & 2 Bathrooms

Accessible 2-BR Suite w/ Tub & 2 Bathrooms
Oconomowoc
The price is HK$1,592
HK$2,056 total
includes taxes & fees
4 Oct - 5 Oct
Accessible 2-BR Suite w/ Tub & 2 Bathrooms

13. Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.6 out of 10, Exceptional, (9 reviews)
"Loved the location and it was just the perfect size for the two of us. Will definitely stay here again when we are in Delafield. "
United States
Becky M.
The price is HK$1,066
HK$1,887 total
includes taxes & fees
19 Oct - 20 Oct
Historic Downtown Luxury-Lake-Coffee-Spa like BA

14. Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.8 out of 10, Exceptional, (12 reviews)
"Comfortable, clean, convenient location and stylish decor. Owner was great! Will recommend to my friends."
United States
Susan D.
The price is HK$1,469
HK$2,493 total
includes taxes & fees
12 Oct - 13 Oct
Historic Downtown- King Bed-St Johns Acad-Shopping

15. Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.8 out of 10, Exceptional, (6 reviews)
"The house worked out just perfect for us! The surrounding grounds are beautiful also. A’Lisa was a very nice host and very easy to get into contact with. We will definitely be back!"
United States
Jon S.
The price is HK$2,432
HK$3,202 total
includes taxes & fees
29 Sept - 30 Sept
Relax & Reboot in this Charming 2-Bedroom Townhome

16. 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, (39 reviews)
"Great place and very clean"
United States
Jason d.
The price is HK$1,306
HK$2,859 total
includes taxes & fees
24 Sept - 25 Sept
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

17. Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (8 reviews)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is HK$1,301
HK$2,294 total
includes taxes & fees
21 Oct - 22 Oct
Historic Downtown-Old World Charm-Dining-Coffee

18. 3BR Home Near Hahns Lake – Newly Updated Kitchen

3BR Home Near Hahns Lake – Newly Updated Kitchen
Johnson Creek
10.0 out of 10, Exceptional, (1 review)
"House is great. Host was excellent when responding to any questions. FYI the bedrooms and bathroom were upstairs. Enjoy our time very much."
United States
D M.
The price is HK$1,262
HK$2,647 total
includes taxes & fees
29 Sept - 30 Sept
3BR Home Near Hahns Lake – Newly Updated Kitchen

19. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Milwaukee WI
9.6 out of 10, Exceptional, (37 reviews)
"I will definitely stay again"
United States
Anonymous traveller
The price is HK$571
HK$646 total
includes taxes & fees
19 Oct - 20 Oct
1 Queen Bed | Non-Smoking, Kitchen

20. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!
Hubertus
9.8 out of 10, Exceptional, (27 reviews)
"We had a wonderful stay! It was the perfect Thanksgiving getaway for our family. "
United States
Mikaela M.
The price is HK$2,149
HK$6,115 total
includes taxes & fees
27 Sept - 28 Sept
Eclectic Hubertus Home w/ Game Room & Fire Pit!
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 8br year round 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 Beautiful Historic Tudor Mansion with sandy Private Beach and Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!.

How many holiday rentals are there in Oconomowoc?

With 25 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 Arts Center and Theatre On Main. Other places in town to visit include Lake Okauchee and Upper Nemahbin Lake.

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.