Book Holiday Homes in Oconomowoc

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Featured Holiday Homes in Oconomowoc

Cozy private cabin on a quiet lake with your own beach.

Cozy private cabin on a quiet lake with your own beach.

Elkhorn WI
Stay at this family-friendly holiday home in Elkhorn. Enjoy free Wi-Fi, an in-room coffee maker and air conditioning. Popular attractions Lake Wandawega and ...
Opens in a new windowCozy private cabin on a quiet lake with your own beach.
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

Waterford WI
Stay at this family-friendly holiday home in Waterford. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Edgewood Golf Course and Green ...
Opens in a new windowCottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan
Iron Ore Retreat: Near Oconomowoc Wedding Venues, Downtown & Lakes

Iron Ore Retreat: Near Oconomowoc Wedding Venues, Downtown & Lakes

Oconomowoc WI
Stay at this holiday home in Oconomowoc. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Theatre On Main and Oakbrook-Eser Studios and ...
Opens in a new windowIron Ore Retreat: Near Oconomowoc Wedding Venues, Downtown & Lakes
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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 WI
Stay at this holiday home in Waukesha. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Monkey Joe's and Prairieville Park are located ...
Opens in a new windowModern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
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 WI
Stay at this holiday home in Waterford. Enjoy a garden, laundry facilities and patios. Popular attractions Green Meadows Petting Farm and Edgewood Golf Course ...
Opens in a new windowRelaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
4 Bdrm 4 Bath Lake front Lake Sinissippi home

4 Bdrm 4 Bath Lake front Lake Sinissippi home

Juneau WI
Stay at this family-friendly holiday home in Juneau. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Sinissippi Lake and Neider Park are ...
Opens in a new window4 Bdrm 4 Bath Lake front Lake Sinissippi home
Lakefront Views + Walk to Dining | Kayaks + Firepit

Lakefront Views + Walk to Dining | Kayaks + Firepit

Pewaukee WI
Stay at this family-friendly holiday home in Pewaukee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pewaukee Lake and Springs Water ...
Opens in a new windowLakefront Views + Walk to Dining | Kayaks + Firepit
Remodeled Home on Wooded Nagawicka Lake Channel

Remodeled Home on Wooded Nagawicka Lake Channel

Delafield WI
Stay at this family-friendly holiday home in Delafield. Enjoy a garden, laundry facilities and patios. Popular attractions Dickten Park and Hawks Inn are located ...
Opens in a new windowRemodeled Home on Wooded Nagawicka Lake Channel
Private estate with tennis court and more

Private estate with tennis court and more

West Bend WI
Stay at this family-friendly holiday home in West Bend. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions West Bend Country Club and Fox ...
Opens in a new windowPrivate estate with tennis court and more
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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
183 Holiday Homes
Lowest Price
NZ$200
Highest Price
NZ$247
Popular accommodation
Cozy private cabin on a quiet lake with your own beach., Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan, Iron Ore Retreat: Near Oconomowoc Wedding Venues, Downtown & Lakes, Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub, Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River, 4 Bdrm 4 Bath Lake front Lake Sinissippi home , Lakefront Views + Walk to Dining | Kayaks + Firepit, Remodeled Home on Wooded Nagawicka Lake Channel, Private estate with tennis court and more

Top trending hotels in Oconomowoc

Staybridge Suites Milwaukee West-Oconomowoc by IHG

Staybridge Suites Milwaukee West-Oconomowoc by IHG

3 out of 5
1141 Blue Ribbon Drive Oconomowoc WI
Fully refundable
The price is NZ$211 per night from 14 May to 15 May
NZ$211
14 May - 15 May
includes taxes & fees
Stay at this hotel in Oconomowoc. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowStaybridge Suites Milwaukee West-Oconomowoc by IHG
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 NZ$224 per night from 17 May to 18 May
NZ$224
17 May - 18 May
includes taxes & fees
Stay at this business-friendly hotel in Oconomowoc. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Oconomowoc Arts Center and ...
Opens in a new windowHilton Garden Inn Oconomowoc
TownePlace Suites by Marriott Oconomowoc

TownePlace Suites by Marriott Oconomowoc

3 out of 5
1242 CORPORATE CENTER DRI Oconomowoc WI
Fully refundableReserve now, pay when you stay
The price is NZ$247 per night from 24 May to 25 May
NZ$247
24 May - 25 May
includes taxes & fees
Stay at this hotel in Oconomowoc. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Oconomowoc Arts Center and Imagination Station are located ...
Opens in a new windowTownePlace Suites by Marriott Oconomowoc
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Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 10 May to 11 May
NZ$200
10 May - 11 May
includes taxes & fees
Stay at this golf hotel in Brookfield. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSheraton Milwaukee Brookfield Hotel
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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.

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^Subject to availability and chosen travel dates.