Pewaukee holiday rentals

We found 1,062 holiday rentals — enter your dates for availability
Discover a selection of 19 homes and other holiday rentals in Pewaukee that are perfect for your trip. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and cable TV. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Pewaukee

Showing deals for:25 Dec - 1 Jan

Living area
Living area
Private kitchen
Dining
Exceptional
(12 reviews)

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc

9% off
AU$34,957
for 7 nights, 1 home
AU$4,994 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
Interior
Outdoor dining
Living area
Dining
Exceptional
(6 reviews)

Skyline House on the Hill - Downtown Milwaukee

Milwaukee

8% off
AU$11,347
for 7 nights, 1 home
AU$1,621 per night
includes taxes & fees
Skyline House on the Hill - Downtown Milwaukee
Neighborhood coffee roaster 4 blocks away. Try an award-winning Nitro cold brew.
Dining room has decorative fireplace, bar cart, and a variety of drinkware.
Dead Bird Brewery, only 3 blocks away — has vintage arcade games and vegan food.
Front living room seating with view to front yard.
Exceptional
(45 reviews)

Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side

Milwaukee

11% off
AU$8,160
for 7 nights, 1 home
AU$1,166 per night
includes taxes & fees
Spacious house, yard, hot tub & games — 1 mile to Downtown and the East Side
Private kitchen
Terrace/patio
Living area
Dining
Exceptional
(8 reviews)

Brady St Retreat! 4BR House w Patio & Fenced Yard

Milwaukee

6% off
AU$4,172
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
Brady St Retreat! 4BR House w Patio & Fenced Yard
Pier and frontage
Great room with reclining leather furniture.
6-burner gas stove, oversized fridge, dishwasher, beverage fridge and microwave.
Outdoor patio area with table and chairs
Exceptional
(73 reviews)

Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room

Pewaukee

8% off
AU$4,159
for 7 nights, 1 home
AU$594 per night
includes taxes & fees
Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room
Exterior
Private kitchen
Interior
Interior
Exceptional
(49 reviews)

Beach House

Lake Mills

8% off
AU$2,928
for 7 nights, 1 home
AU$418 per night
includes taxes & fees
Beach House
Living area
Living area
Dining
Private kitchen
Exceptional
(27 reviews)

Oak Park Bliss: 3BR, 2BA Gem

Milwaukee

7% off
AU$6,563
for 7 nights, 1 home
AU$938 per night
includes taxes & fees
Oak Park Bliss: 3BR, 2BA Gem
Interior
Private kitchen
Room
Interior
Exceptional
(24 reviews)

Cottage near Mt. Mary College

Milwaukee

7% off
AU$3,548
for 7 nights, 1 cottage
AU$507 per night
includes taxes & fees
Cottage near Mt. Mary College
Exterior detail
Outdoor dining
Room
Interior
Exceptional
(12 reviews)

Gorgeous space with huge porch.

Milwaukee

7% off
AU$2,265
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Gorgeous space with huge porch.
Private kitchen
Exterior
Living area
Property grounds
Exceptional
(33 reviews)

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Wales

8% off
AU$7,083
for 7 nights, 1 home
AU$1,012 per night
includes taxes & fees
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Property grounds
Property grounds
Private kitchen
Property grounds
Exceptional
(27 reviews)

Spacious Rustic Log Home Retreat Near Madison & Milwaukee

Johnson Creek

8% off
AU$3,402
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
Spacious Rustic Log Home Retreat Near Madison & Milwaukee
Exterior
Living area
Dining
Private kitchen
Exceptional
(26 reviews)

Green Valley Homes - 2 BDRM Lower Apartment

Milwaukee

7% off
AU$2,050
for 7 nights, 1 home
AU$293 per night
includes taxes & fees
Green Valley Homes - 2 BDRM Lower Apartment
Terrace/patio
Exterior
Living area
Private kitchen
Exceptional
(18 reviews)

Milwaukee Bayview Getaway with Private Hot Tub

Milwaukee

7% off
AU$6,265
for 7 nights, 1 home
AU$895 per night
includes taxes & fees
Milwaukee Bayview Getaway with Private Hot Tub
Interior
Living area
Room
Interior
Exceptional
(13 reviews)

Charming 3-bedroom lake house in serene Richfield!

Hubertus

9% off
AU$4,270
for 7 nights, 1 home
AU$610 per night
includes taxes & fees
Charming 3-bedroom lake house in serene Richfield!
Dining
Exterior
Outdoor spa tub
Living area
Exceptional
(34 reviews)

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee

7% off
AU$3,271
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
The Gem of Brewers Hill with hot tub and seasonal pool
Master Bedroom with Ensuite Bath.
House in Fall/Winter.
Sliding Glass Doors leading to Deck.
Roku T.V. in Living Room.
Exceptional
(19 reviews)

Whitefish Bay 3Bedroom Entire House Sleeps 4

Milwaukee

14% off
AU$2,586
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Whitefish Bay 3Bedroom Entire House Sleeps 4
Private kitchen
Living area
Dining
Interior
Excellent
(24 reviews)

Spacious 4-bedroom home in quiet neighborhood

Milwaukee

8% off
AU$1,780
for 7 nights, 1 home
AU$254 per night
includes taxes & fees
Spacious 4-bedroom home in quiet neighborhood
Private kitchen
Living area
Room
Dining
Exceptional
(17 reviews)

Spacious house, 8 mins downtown Sleeps 8 guests. Backyard

Milwaukee

7% off
AU$4,126
for 7 nights, 1 home
AU$589 per night
includes taxes & fees
Spacious house, 8 mins downtown Sleeps 8 guests. Backyard
Dining
Interior
Private kitchen
Lobby
Exceptional
(18 reviews)

Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking

Milwaukee

7% off
AU$4,567
for 7 nights, 1 apartment
AU$652 per night
includes taxes & fees
Huge condo in historic hotel near Lake Michigan/Parks/Festivals w/parking
Private kitchen
Exterior
Interior
Room
Exceptional
(5 reviews)

Stylish Studio in Walkers Point

Milwaukee

11% off
AU$1,773
for 7 nights, 1 apartment
AU$253 per night
includes taxes & fees
Stylish Studio in Walkers Point
Living area
Terrace/patio
Interior
Private kitchen
Exceptional
(17 reviews)

Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side

Milwaukee

7% off
AU$4,195
for 7 nights, 1 home
AU$599 per night
includes taxes & fees
Spacious 3BR/2BA Townhome w/ Private Parking & Walkable East Side
Cozy living room with leather sofa, wood floors, and stylish dark accents
Exterior
Cozy modern bedroom with luxe white bedding and warm designer touches
Private kitchen
Exceptional
(5 reviews)

Stylish Apt in Walker's Point

Milwaukee

12% off
AU$2,342
for 7 nights, 1 apartment
AU$335 per night
includes taxes & fees
Stylish Apt in Walker's Point

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the friendly city of Pewaukee

The lake and other outdoor surroundings create an inviting atmosphere in Pewaukee. This welcoming city is known for its water park, restaurants and sporting events. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Pewaukee

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Pewaukee a fun spot to go on holiday. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Springs Water Park (2.4 mi / 3.9 km)
  • Milwaukee County Zoo (11.6 mi / 18.7 km)
  • Milwaukee Mile Speedway (13.3 mi / 21.4 km)
  • Erin Hills Golf Course (13.7 mi / 22.1 km)
  • Cabela's (14.2 mi / 22.8 km)
  • Ray's MTB Indoor Mountain Bike Park (14.3 mi / 23.1 km)

Exploring the natural features in Pewaukee

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Pewaukee is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Pewaukee Lake Beach (0.3 mi / 0.5 km)
  • Pewaukee Lake (2.4 mi / 3.8 km)
  • Holy Hill (11.8 mi / 19 km)
  • Lac La Belle (13.4 mi / 21.6 km)
  • Boerner Botanical Gardens (15.3 mi / 24.6 km)
  • Mitchell Park Horticultural Conservatory (16.3 mi / 26.3 km)

Transport to and around Pewaukee

The nearest airport is in Waukesha, WI (UES-Waukesha County), located 3.2 mi (5.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Milwaukee, WI (MKE-General Mitchell Intl.), which is 20.3 mi (32.7 km) away.

Frequently asked questions

What is the best area to stay in Pewaukee when booking a holiday rental?
When considering a holiday rental in Pewaukee, Wisconsin, the area surrounding the lake is one of the best choices. This scenic neighbourhood offers stunning views and a tranquil atmosphere, making it great for a relaxing getaway. Here, you'll find a variety of properties, from charming lakeside cottages to modern family homes, suiting different tastes and budgets.Staying near Pewaukee Lake not only grants easy access to the water for activities like boating and fishing, but it also places you close to some delightful attractions. The lakefront park is a lovely spot for picnics and leisurely strolls, while the vibrant downtown area features a selection of quaint shops and eateries. Additionally, the nearby Pewaukee Lake Beach is a favourite among locals and visitors alike, providing a wonderful place to soak up the sun during the warmer months.
Where are the best areas for renting a beach house in Pewaukee?
For renting a beach house in Pewaukee, the area surrounding Pewaukee Lake is ideal. This picturesque setting offers a variety of holiday rentals that provide easy access to the lake's sandy shores and recreational activities. Many properties in this region come equipped with amenities such as private docks, outdoor patios, and fully equipped kitchens, making them great for families or groups wanting to enjoy lakeside living.The neighbourhoods along the western shore, particularly near the Pewaukee Lake Park, offer beach houses that allow guests to enjoy the scenic views of the water. Properties in this area often feature spacious living areas, barbecues for outdoor cooking, and sometimes even fire pits for evening gatherings. Additionally, the proximity to local shops, restaurants, and parks enhances the convenience for travellers.For those interested in water sports, rentals near the lake's public access points provide opportunities for boating, fishing, and swimming. Some houses may also offer amenities like kayaks or paddleboards for guests to use during their stay.
What is the most popular type of holiday rental accomodation in Pewaukee?
In Pewaukee, holiday houses are the most popular type of holiday rental, with approximately 57 available throughout the area. These properties often come with generous living spaces, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many holiday houses also feature outdoor areas, such as decks or patios, where guests can relax and enjoy the scenic views of Pewaukee Lake. Additionally, there are several cottages available, offering a quaint and charming alternative for those seeking a cozier, more intimate setting.
Are there any family house rentals in Pewaukee?
In Pewaukee, Wisconsin, there are numerous family-friendly house rentals available—specifically around 16 options scattered throughout the area. This charming lakeside town is superb for families seeking both relaxation and adventure. Many of these homes boast spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces where children can play or where families can enjoy barbecues together.Properties near Pewaukee Lake often offer amenities like private docks for boating or fishing, while some may even feature game rooms for indoor entertainment. The area is also close to local parks, playgrounds, and walking trails, providing ample opportunities for outdoor activities.
Are there pet-friendly house rentals in Pewaukee?
In Pewaukee, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. Many of these properties are conveniently located near Pewaukee Lake, offering easy access to outdoor activities such as swimming, fishing, and boating. The rentals often come with amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, providing a homely atmosphere for families and groups.The surrounding areas also feature parks like the Pewaukee Lake Park, which has walking trails and picnic spots, superb for enjoying the outdoors with pets. Additionally, the nearby village offers charming cafes and shops that welcome pets, enhancing the overall experience for both you and your furry friends.
Are there any remote work holiday rentals in Pewaukee?
In Pewaukee, Wisconsin, there are plenty of remote work-friendly holiday rentals available, with around 60 options to choose from. This picturesque lakeside town provides a conducive environment for those looking to combine work and leisure. Many properties come equipped with essential amenities such as free Wi-Fi, dedicated workspaces with desks and comfortable chairs, ensuring that remote workers can be productive during their stay.The area is known for its charming waterfront, where guests can enjoy scenic views and outdoor activities during breaks. Nearby attractions include the beautiful Pewaukee Lake, which offers opportunities for fishing, boating, and relaxing by the shore. The local dining scene features a variety of establishments ranging from casual cafes to more upscale restaurants, making it easy to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pewaukee?
In Pewaukee, popular rental amenities include kitchens, which allow guests to prepare their own meals at their convenience. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the fresh air. Onsite parking is another common amenity, making it convenient for travellers with vehicles. Additionally, some rentals may come equipped with blenders, great for those looking to whip up smoothies or other beverages during their stay.
When is the best time to visit Pewaukee for a holiday rental?
The best time to visit Pewaukee for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period attracts those looking to enjoy the beautiful lakeside setting, engage in outdoor activities like swimming and boating, and take advantage of the warm weather.In July, you can expect delightful temperatures averaging around 24 to 30 degrees Celsius, creating a great environment for sun-soaked days by the lake. The atmosphere is bustling with summer events, including music festivals and local markets, making it an ideal time for families and friends seeking a lively getaway.For those who prefer a quieter experience, consider planning your visit in October when the summer crowds have dispersed. This month offers a serene escape with the added charm of autumn foliage, great for leisurely walks along the scenic trails and enjoying the crisp air.Ultimately, the best time to book your holiday rental in Pewaukee depends on your preference for a lively summer atmosphere or a peaceful autumn retreat.
What are the top attractions in Pewaukee?
In Pewaukee, visitors can enjoy a range of attractions centred around its picturesque lake. Pewaukee Lake itself is a prime spot for swimming, boating, and fishing, with several parks along its shores offering picnic areas and playgrounds for families. The nearby Pewaukee Lake Beach is particularly popular during the summer months, providing a sandy area for sunbathing and water activities.For outdoor enthusiasts, the Lake Pewaukee Park features trails for walking and biking, as well as facilities for sports like volleyball and basketball. The charming downtown area offers local shops, cafes, and restaurants where visitors can experience the community's friendly atmosphere.In addition, the nearby Retzer Nature Centre provides opportunities for hiking and wildlife observation, showcasing the natural beauty of the region.
Are all fees included in the Pewaukee holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pewaukee holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pewaukee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pewaukee holiday homes?
You can find great discounts on holiday homes in Pewaukee on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pewaukee holiday home booking on Stayz?
To find Pewaukee holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pewaukee?
A long-stay holiday home in Pewaukee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pewaukee holiday home?
Book your Pewaukee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pewaukee?
Prices for holiday homes in Pewaukee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pewaukee to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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