Oconomowoc Vacation Rentals

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Vacation Rentals in Oconomowoc

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

Richfield WI

Located in Hubertus, this vacation home is on a lake, a 2-minute drive from Heiliger Huegel Ski Club and 6 minutes from Holy Hill.

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

Waukesha WI

$282 nightly

$319 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at this vacation home in Waukesha, you'll be within a 5-minute drive of Monkey Joe's and Prairieville Park.

Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!

Oconomowoc WI

Located in Oconomowoc, this vacation home is on the waterfront, a 3-minute drive from Aurora Medical Center Summit and 6 minutes from Oconomowoc Memorial Hospital.

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

New Berlin WI

$1,610 nightly

$1,819 total

Dec 22 - Dec 23

Total with taxes and fees

With a stay at this vacation home in New Berlin, you'll be within a 10-minute drive of Waukesha Springs Park and Minooka Park.

Serene 4-bedroom Lake House in Pewaukee-Hot Tub!

Pewaukee WI

With a stay at this vacation home in Pewaukee (Starke Peninsula), you'll be a 1-minute drive from Pewaukee Lake and 5 minutes from Two Brothers Wines.

Erin Hills Area Perfect Getaway - NEW Fall Color and Winter Pricing!

Rubicon WI

Located in Rubicon, this vacation home is in a rural location, within a 15-minute drive of Erin Hills Golf Course and Heiliger Huegel Ski Club.

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Sussex WI

Located in Sussex, this vacation home is a 1-minute drive from Menomonee Park and 8 minutes from Town Hall Clinic.

LAKEFRONT HIDDEN GEM !

Elkhorn WI

Located in Elkhorn, this vacation home is on the waterfront, a 1-minute drive from Lake Wandawega and 5 minutes from Evergreen Golf Club.

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

Hartford WI

$783 nightly

$881 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home in Hartford, you'll be within a 5-minute drive of Hartford City Hall and Wisconsin Automotive Museum.

4 Bdrm 4 Bath Lake front Lake Sinissippi home

Juneau WI

Located in Juneau, this vacation home is on the waterfront, within a 15-minute drive of Sinissippi Lake and Neider Park.

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Hubertus WI

Located in Hubertus, this vacation home is on a lake, a 4-minute drive from Heiliger Huegel Ski Club and 8 minutes from Holy Hill.

Relax Near Everything in Milwaukee

Wauwatosa WI

With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 15-minute drive of American Family Field and The Rave-Eagles Club.

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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.