Book Holiday Homes in Oconomowoc

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Featured Holiday Homes in Oconomowoc

Beautiful lakefront, Newly Remodeled Lower Level! ^^

Beautiful lakefront, Newly Remodeled Lower Level! ^^

Hustisford
With a stay at this vacation home in Hustisford, you'll be on the waterfront, just steps from Sinissippi Lake and a 3-minute drive from Neider Park.
Beautiful lakefront, Newly Remodeled Lower Level! ^^
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Waterford
Located in Waterford, this vacation home is on the waterfront, within a 15-minute drive of Jean Jacobson Dog Park and Green Meadows Petting Farm.
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Eclectic Hubertus Home w/ Game Room & Fire Pit!

Eclectic Hubertus Home w/ Game Room & Fire Pit!

Hubertus
Located in Hubertus, this vacation home is within a 15-minute drive of Heiliger Huegel Ski Club and Holy Hill.
Eclectic Hubertus Home w/ Game Room & Fire Pit!
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Newly Renovated Lakefront Cottage, Peaceful, Cozy Modern Farmhouse ~Dog Friendly

Newly Renovated Lakefront Cottage, Peaceful, Cozy Modern Farmhouse ~Dog Friendly

Waterford
The price is AU$726 per night from 26 Dec to 27 Dec
AU$726
includes taxes & fees
26 Dec - 27 Dec
When you stay at this vacation home in Waterford, you'll be on the waterfront and 13 minutes by car from Edgewood Golf Course.
Newly Renovated Lakefront Cottage, Peaceful, Cozy Modern Farmhouse ~Dog Friendly
 Modern lake house with a double lot. The views are amazing inside and out!

Modern lake house with a double lot. The views are amazing inside and out!

Wind Lake
The price is AU$958 per night from 27 Dec to 28 Dec
AU$958
includes taxes & fees
27 Dec - 28 Dec
With a stay at this vacation home in Waterford, you'll be within a 15-minute drive of Edgewood Golf Course and Martin's Woods State Natural Area.
Modern lake house with a double lot. The views are amazing inside and out!
Amazing Five Bedroom Milwaukee Vacation Home!!

Amazing Five Bedroom Milwaukee Vacation Home!!

Sussex
Located in Sussex, this vacation home is within a 10-minute drive of Town Hall Clinic and Froedtert Menomonee Falls Hospital.
Amazing Five Bedroom Milwaukee Vacation Home!!
Modern Lake House: Sandy Floor, Breathtaking Views

Modern Lake House: Sandy Floor, Breathtaking Views

Wind Lake
Located in Waterford, this vacation home is on a lake, within a 15-minute drive of Jean Jacobson Dog Park and Little Muskego Lake.
Modern Lake House: Sandy Floor, Breathtaking Views
Beautiful Waukesha Home

Beautiful Waukesha Home

Waukesha
The price is AU$875 per night from 31 Dec to 1 Jan
AU$875
includes taxes & fees
31 Dec - 1 Jan 2025
A stay at this vacation home places you in the heart of Waukesha, a 5-minute drive from Glacial Drumlin Bike Trail and 5 minutes from Waukesha County ...
Beautiful Waukesha Home
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

dousman
With a stay at this vacation home in Dousman, you'll be on the waterfront, and 8.3 mi (13.3 km) from Palmyra Beach and 8.4 mi (13.6 km) from Kettle Moraine ...
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!
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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.

Oconomowoc Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oconomowoc vacation homes are the perfect way for you to wing it.

Holiday houses in Oconomowoc let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oconomowoc in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oconomowoc adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oconomowoc with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oconomowoc vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oconomowoc Holiday Homes essential information

Accommodation
148 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$958
Popular accommodation
Beautiful lakefront, Newly Remodeled Lower Level! ^^, Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River, Eclectic Hubertus Home w/ Game Room & Fire Pit!, Newly Renovated Lakefront Cottage, Peaceful, Cozy Modern Farmhouse ~Dog Friendly, Modern lake house with a double lot. The views are amazing inside and out! , Amazing Five Bedroom Milwaukee Vacation Home!!, Modern Lake House: Sandy Floor, Breathtaking Views, Beautiful Waukesha Home, Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

Top trending hotels in Oconomowoc

Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel

Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel

3 out of 5
1141 Blue Ribbon Drive, Oconomowoc, WI
Fully refundable
The price is AU$233 per night from 26 Dec to 27 Dec
AU$233
includes taxes & fees
26 Dec - 27 Dec
Located in Oconomowoc, Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel is a 2-minute drive from Aurora Medical Center Summit and 5 minutes from Oconomowoc ...
Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel
Hilton Garden Inn Oconomowoc

Hilton Garden Inn Oconomowoc

3 out of 5
1443 Pabst Farms Cir, Oconomowoc, WI
Fully refundableReserve now, pay when you stay
The price is AU$198 per night from 5 Jan to 6 Jan
AU$198
includes taxes & fees
5 Jan - 6 Jan 2025
When you stay at Hilton Garden Inn Oconomowoc in Oconomowoc, you'll be near the airport, within a 5-minute drive of Aurora Medical Center Summit and Oconomowoc ...
Hilton Garden Inn Oconomowoc
TownePlace Suites by Marriott Oconomowoc

TownePlace Suites by Marriott Oconomowoc

2.5 out of 5
1242 CORPORATE CENTER DRI, Oconomowoc, WI
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 12 Jan to 13 Jan
AU$202
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Oconomowoc, TownePlace Suites by Marriott Oconomowoc is within a 5-minute drive of Aurora Medical Center Summit and Oconomowoc Memorial Hospital.
TownePlace Suites by Marriott Oconomowoc
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Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 30 Dec to 31 Dec
AU$156
includes taxes & fees
30 Dec - 31 Dec
With a stay at Sonesta Milwaukee West Wauwatosa in Milwaukee (Wauwatosa), you'll be a 3-minute drive from Milwaukee County Zoo and 6 minutes from Wisconsin Exposition ...
Sonesta Milwaukee West Wauwatosa
Don't see what you're looking for?
See all available properties in Oconomowoc
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.