Book Holiday Homes in Pewaukee
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Pewaukee
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
With a stay at this vacation home in Waukesha, you'll be within a 5-minute drive of Monkey Joe's and Prairieville Park.
Family Paradise 3 bedroom, Cozy Home + Game Room.
Brown Deer WI
The price is AU$477 per night from 20 Dec to 21 Dec
AU$477
20 Dec - 21 Dec
includes taxes & fees
With a stay at this vacation home in Milwaukee (Brown Deer), you'll be within a 10-minute drive of Lake Michigan and Walter Schroeder Aquatic Center.
Save an average of 15% on thousands of hotels when you're signed in
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 ...
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Milwaukee WI
The price is AU$666 per night from 19 Dec to 20 Dec
AU$666
19 Dec - 20 Dec
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Charming Vintage Farmhouse 1 bedroom Garden Oasis
Milwaukee WI
With a stay at this vacation home in Milwaukee (Bay View), you'll be a 1-minute drive from Lake Michigan and 8 minutes from Fiserv Forum.
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18
New Berlin WI
The price is AU$2,774 per night from 22 Dec to 23 Dec
AU$2,774
22 Dec - 23 Dec
includes taxes & 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.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
River Hills WI
With a stay at this vacation home in Milwaukee, you'll be within a 15-minute drive of Lake Michigan and Fiserv Forum.
Remodeled Home - Steps from Brady Street!
Milwaukee WI
The price is AU$407 per night from 7 Jan to 8 Jan
AU$407
7 Jan - 8 Jan 2026
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
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.
Pewaukee 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 Pewaukee vacation homes are the perfect way for you to wing it.
Holiday houses in Pewaukee 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 Pewaukee 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 Pewaukee adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Pewaukee 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 Pewaukee 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.
Pewaukee Holiday Homes essential information
Accommodation | 469 Holiday Homes |
|---|---|
Lowest Price | AU$152 |
Highest Price | AU$2,774 |
Popular accommodation | NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby, Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub, Family Paradise 3 bedroom, Cozy Home + Game Room., Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!, Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find, Charming Vintage Farmhouse 1 bedroom Garden Oasis, 17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18, Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!, Remodeled Home - Steps from Brady Street! |
Top trending hotels in Pewaukee
The Ingleside Hotel
2810 Golf Road Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$182 per night from 5 Jan to 6 Jan
AU$182
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Pewaukee, The Ingleside Hotel is within a 10-minute drive of Waukesha County Expo Center and The Corners of Brookfield.
Wildwood Lodge
N14 W24121 Tower Place Pewaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 21 Dec to 22 Dec
AU$152
21 Dec - 22 Dec
includes taxes & fees
Located in Pewaukee, Wildwood Lodge is in the business district, a 4-minute drive from Waukesha County Expo Center and 12 minutes from Milwaukee County Zoo.
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 7 Jan to 8 Jan
AU$271
7 Jan - 8 Jan 2026
includes taxes & fees
With a stay at The Pfister Hotel, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and Fiserv Forum.
Save an average of 15% on thousands of hotels when you're signed in
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$228 per night from 28 Dec to 29 Dec
AU$228
28 Dec - 29 Dec
includes taxes & fees
With a stay at Saint Kate - The Arts Hotel, you'll be centrally located in Milwaukee, within a 10-minute walk of Riverside Theater and Fiserv Forum.
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.
More ways to explore Pewaukee
Top picks
Hotels
- Alexandria Apartment Hotels
- Accommodation in Lorne
- Hotels in Bondi Beach
- Hotels around Jewel Cave
- Hotels in Peregian Beach
- Pet Friendly Hotels in New South Wales
- The Escape in Southern Cross Station
- Accommodation in Melbourne
- Accommodation in Torquay
- Accommodation in Wellington
- Hotels in Covent Garden
- Bayside Hotel
- Accommodation in Anglesea
- Hotels in Melbourne Central Business District
- Motel Northview Mackay
- Holiday Homes Swan Valley
- ibis Styles Orange
- Nanango Pet Friendly Hotels
- Hotels in Ascot
- Accommodation in Cradle Mountain
- Caravan Parks Perisher Valley
- Tasman Holiday Parks - Geelong
- Accommodation in Jindabyne
- Tallarook Motor Inn
Flights
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.