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

Holiday Homes in Oconomowoc

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Oconomowoc holiday homes

A hot tub under a covered area with a wooden roof, surrounded by a white fence, trees, and a clear sky.

1. 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 €306
includes taxes & fees
15 Sept - 16 Sept
Private Hot Tub • Bright Home Near Downtown
A two-story house with a balcony, a front porch, and a visible garage.

2. Chic Retreat Near Wedding Venues + Fire Pit

Chic Retreat Near Wedding Venues + Fire Pit
Oconomowoc
10.0 out of 10, Exceptional, (27 reviews)
"Incredible stay in such a beautiful home! "
United States
Saarah B.
The price is €544
includes taxes & fees
16 Sept - 17 Sept
Chic Retreat Near Wedding Venues + Fire Pit
A deck with a view of a lake, docked boats, and a covered area with a bench.

3. Waterfront Lake Cottage - Upper Nemahbin Lake

Waterfront Lake Cottage - Upper Nemahbin Lake
Peninsular Park
9.6 out of 10, Exceptional, (37 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 €608
includes taxes & fees
8 Sept - 9 Sept
Waterfront Lake Cottage - Upper Nemahbin Lake

4. 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 €349
includes taxes & fees
11 Sept - 12 Sept
Relax & Reboot in this Charming 2-Bedroom Townhome
A modern two-story house with a balcony, a patio with outdoor furniture, and a well-maintained lawn.

5. Well Appointed Home Steps to Pewaukee Lake

Well Appointed Home Steps to Pewaukee Lake
Pewaukee
9.8 out of 10, Exceptional, (19 reviews)
"such a lovely home and great restaurants and stores near by. Looks like a little sea side town in Maine"
United States
Rachel W.
The price is €430
includes taxes & fees
16 Sept - 17 Sept
Well Appointed Home Steps to Pewaukee Lake
A modern kitchen with a large island, stainless steel sink, and pendant lights.

6. 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, (38 reviews)
"Great place and very clean"
United States
Jason d.
The price is €321
includes taxes & fees
9 Sept - 10 Sept
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
A compact kitchenette with a microwave, a small countertop, and a pendant light.

7. 3BR Home Near Hahns Lake – Newly Updated Kitchen

3BR Home Near Hahns Lake – Newly Updated Kitchen
Johnson Creek
The price is €248
includes taxes & fees
29 Sept - 30 Sept
3BR Home Near Hahns Lake – Newly Updated Kitchen
A beach with a view of the water, boats, and a distant shoreline.

8. Spa House by the beach. Pewaukee Lake

Spa House by the beach. Pewaukee Lake
Downtown Pewaukee
9.0 out of 10, Wonderful, (2 reviews)
"Lovely relaxing home. Had a great time. Train traffic can be a bit much especially if you’re a lite sleeper. Overall great experience."
United States
Ryan E.
The price is €391
includes taxes & fees
19 Sept - 20 Sept
Spa House by the beach. Pewaukee Lake
A spacious interior with a stone staircase, a large window, and a cozy seating area.

9. 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 €678
includes taxes & fees
8 Sept - 9 Sept
Eclectic Hubertus Home w/ Game Room & Fire Pit!
A modern kitchen with stainless steel appliances, a granite countertop, and a large window.

10. New: Tremendous 4-bedroom house on private lot in charming Brookfield

New: Tremendous 4-bedroom house on private lot in charming Brookfield
Brookfield
The price is €355
includes taxes & fees
8 Sept - 9 Sept
New: Tremendous 4-bedroom house on private lot in charming Brookfield
A spacious living area with a wooden staircase, a round table with a book and certificates, and a cozy seating area with a sofa and chairs.

11. Historic, 4-bedroom house in charming Hartford

Historic, 4-bedroom house in charming Hartford
Hartford
The price is €772
includes taxes & fees
12 Sept - 13 Sept
Historic, 4-bedroom house in charming Hartford
A staircase with wooden railings and carpeted steps leading to a second floor. A potted plant is placed near the staircase, and a sofa is visible in the foreground.

12. CBI Havens is set in a calm and well‑connected pocket of Milwaukee,

CBI Havens is set in a calm and well‑connected pocket of Milwaukee,
Milwaukee
10.0 out of 10, Exceptional, (1 review)
"It was a very nice play to stay and very welcoming and the hosts was very helpful "
United States
Marianna C.
The price is €553
includes taxes & fees
8 Sept - 9 Sept
CBI Havens is set in a calm and well‑connected pocket of Milwaukee,
A modern kitchen with white cabinetry, granite countertops, a glass dining table, and two chairs.

13. Modern, impeccably styled, a seamless convenience in a prime, quiet location.

Modern, impeccably styled, a seamless convenience in a prime, quiet location.
Milwaukee
The price is €643
includes taxes & fees
8 Sept - 9 Sept
Modern, impeccably styled, a seamless convenience in a prime, quiet location.
A two-story red house with a fire pit and outdoor seating.

14. The Red Lodge - Unique Gem Near Lakes with Game Room and Hot Tub!

The Red Lodge - Unique Gem Near Lakes with Game Room and Hot Tub!
Elkhorn
10.0 out of 10, Exceptional, (23 reviews)
"The five of us had a great time. Very clean place, and extremely responsive host. I'd highly recommend this place!"
United States
Mathew W.
The price is €955
includes taxes & fees
18 Sept - 19 Sept
The Red Lodge - Unique Gem Near Lakes with Game Room and Hot Tub!
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.
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Top Oconomowoc Hotel Reviews

Hilton Garden Inn Milwaukee Northwest Conference Center

Hilton Garden Inn Milwaukee Northwest Conference Center

8/10 Good
"The room was clean however the shampoo bottle was super Empty other wise I would rate 5 star on-this place."
Sydney 1-night trip
Posted 8 hours ago
Hilton Garden Inn Milwaukee Northwest Conference Center

Find out more about Oconomowoc

Oconomowoc Holiday Homes information

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