Holiday rentals in Waukesha
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Quick stats about holiday rentals in Waukesha
Total holiday rentals
Explore 50 holiday rentals in Waukesha
Nightly prices starting at
Waukesha holiday rentals start at $39 SGD per night before taxes and fees
Verified guest reviews
Over 1,600 verified reviews to help you choose
Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
50 of Waukesha holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Waukesha rentals
4.7 Average rating
Waukesha stays receive an average rating of 4.7 out of 5 from guests
Top-rated holiday rentals in Waukesha
Guests agree: these stays are highly rated for location, cleanliness and more.
★Cozy Beach Themed Home★2 Beds★Spacious Parking★
Cozy and quaint two bedroom beach themed home located in the heart of West Allis. Close to public transportation and a few minutes driving to State Fair Park, Milwaukee County Zoo, Potawatomi Hotel & Casino, bars, restaurants, and more! Peaceful and quiet residential spot with plenty of parking on premises (up to 3 cars.) Amenities include: Spacious Parking, Smart TV, WiFi, Self Check in, Fresh Sheets & Towels, Hairdryer, Fully Stocked Kitchen, Washer & Dryer, Reading Material and much more!
Pet-Friendly Retreat•Sleeps 8•Huge Yard•Fire pit
Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.
Lake, Sauna, Hot Tub, Gym, Fire Pit, Kayak+More
Brought to you by NCL Properties, this serene getaway is designed for relaxation, restoration, and a laid back lake vibe. Wake up to lake views, sip your morning brew from our coffee bar, and let the calm energy of the water set the tone for your stay. Unwind in the hot tub, or infrared sauna for a soothing reset. We also have a dedicated fitness corner features a Peloton. Spend your days lounging on the deck, kayaking, or soaking in the peaceful setting that makes Pewaukee lake so special.
Tucked Away
For those in need of a "home away from home" while on the road working or just passing though on your travels. This private, quaint backyard parking/entrance mini apartment located in Waukesha's "Historic District" is for you. Enjoy large outer deck as weather permits. Stairs are required outside to enter unit. Walking distance to downtown area. Easy access from this location to Madison (65 miles) and Milwaukee (12 miles). Located near Carroll University and Waukesha Memorial Hospital.
Lake Country Retreat| Shared Pier Access|Lake View
Just steps from the shores of Lake Nagawicka, this cozy home offers the perfect blend of relaxation and adventure. Enjoy a shared pier for kayaking, paddleboarding, or lakeside lounging. Minutes from downtown Delafield and endless activities. Rent from our preferred boat partner or bring your own, boat slip available for minimal cost. Ideal for couples or small families. Whether you’re looking to unwind, explore, or make lasting memories by the water, this inviting getaway has it all.
Nagawicka Woods-Beautiful Lake Country Ranch Home
Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.
The Loft @ The Butler Place. 1846 homestead.
The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.
Inlaw Suite with Downtown Charm
Unbeatable Historic Downtown location. Duplex-like entry to your key-access 300sf downstairs suite, full kitchen/bath, standard queen bed w/ memory foam mattress. Walk a quiet neighborhood, <1 mile to the art hub of downtown - enjoy the summer farmer's market, or walk along Fox River! Minutes from convenience/department stores/more parks, 10 mins to I-94, <20 min to Pewaukee lake, <30 mins to Milwaukee/ airport/Lake Michigan. *NOTE: Ceiling is 6ft 7 inches.* NOTE: No pets allowed.*
2-acre retreat steps from Nagawicka Lake
Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.
Garden Retreat in law Suite
Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.
Designer Home with Upper Balcony & Lake Views
Experience Lake Country luxury in this designer retreat overlooking Pewaukee Lake. Steps from the beach and downtown dining, the home features panoramic water views, a chef-grade kitchen, and spa-style bathrooms with heated floors. Perfect for weddings, business trips, or a quiet escape, it’s your private sanctuary in the heart of Pewaukee. This home is part of another rental, yet offers private entries and minimal shared wall space for a quiet, comfortable stay.
Luxury Delafield Retreat | Walk to Lake & Shops!
⭐ 5-Star Comfort | Prime Location |Historic Downtown| Self Check-In ⭐ Welcome to Your Ultimate Delafield Getaway! Nestled in the heart of Historic Downtown Delafield, this luxury apartment is steps from Lake Nagawicka, top-rated restaurants, boutique shops, and scenic parks. Designed for both relaxation and adventure, this stylish retreat offers modern comforts, high-end finishes, and a perfect location for exploring everything Delafield has to offer.
Popular amenities for Waukesha holiday rentals
Stay near Waukesha's top sights
Other great holiday rentals in Waukesha
2BR Sapphire Summit Suite w/ Bar – Brookfield
All the Pleasures of Home
Historic Walker’s Point Home • Sleeps 10 • Garage
Bright 3BR Near Zoo & Downtown| Sleeps 6 | Parking
Beautiful safe quiet home in great location
Beautiful Home in Waukesha
Brand New Studio w. Private Entry + Garden Patio
Cozy Little House in Waukesha, Wisconsin
When is the best time to visit Waukesha?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD | $180 SGD |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
What are the best places to stay in Waukesha?
Stays in downtown Waukesha provide easy access to dining, shops, and cultural sites, while neighborhoods near parks appeal to those seeking more outdoor space. Family travelers often opt for residential areas known for their welcoming atmosphere.
What are the best things to do in Waukesha with kids?
Waukesha has playgrounds, creative spaces in parks, and riverfront trails that families often explore. Frame Park’s playground is frequently suggested, and seasonal events create welcoming activities around the city for younger visitors.
What are some of the best things to do in Waukesha?
Explore downtown’s historic architecture, stroll the riverwalk, or visit local art galleries and markets. Frame Park is frequently suggested for garden walks, while area trails appeal to those looking for outdoor activity.
How is the weather in Waukesha?
Waukesha experiences cold winters, with temperatures from 17°F to 36°F (-8°C to 2°C), and warm summers near 65°F to 82°F (18°C to 28°C). Rain is spread across the year, with spring and summer months often seeing higher precipitation. Bring clothing suitable for seasonal changes.
When is the best time to visit Waukesha?
Late spring through early fall is often recommended for comfortable temperatures, blooming parks, and an uptick in community events. Winter travelers can anticipate colder weather and a quieter atmosphere, with opportunities to experience seasonal traditions.
What are the best places to visit in Waukesha?
Frame Park, the Waukesha County Historical Society and Museum, and the city’s downtown riverwalk are some of the most popular sites. Art spaces and local theaters add cultural variety to your visit.
What are some hiking trails in Waukesha?
Walkers and hikers frequently explore the Glacial Drumlin State Trail and Fox River Trail for scenic views and a peaceful atmosphere. Frame Park’s loop also provides a gentle path along gardens and riverbank.
What are some family activities we can do in Waukesha?
Families often enjoy the hands-on exhibits at the local children’s museum, exploring Frame Park’s play areas, or discovering interactive public art downtown. Outdoor spaces around Waukesha provide room for both relaxation and play.
What are some of the best day trip ideas from Waukesha?
Consider exploring the Milwaukee lakefront for museums and public markets, or discover local nature preserves and neighboring small towns with historic charm. Outdoor enthusiasts might seek out regional parks that are known for hiking and lakeside recreation.
Are there any pet friendly accommodations available in Waukesha?
Waukesha has pet-friendly vacation rentals and stays, particularly in downtown and residential neighborhoods. Local parks and walking trails make outings with your dog convenient and enjoyable.
What are some local tips for visiting Waukesha?
Locals frequently recommend checking out seasonal farmers markets and taking a stroll along the riverwalk for community art and historic views. Keep an eye on event calendars for festivals, especially in warmer months.
What is Waukesha known for?
Waukesha is known for its historic downtown, abundance of local parks, and contributions to music history as the birthplace of Les Paul. Community-focused festivals and public art are also key parts of its local identity.
What are the best hidden gems to explore in Waukesha?
Explore Frame Park for scenic riverfront gardens and tranquil walking paths. The city also has local art studios and historic buildings tucked around downtown, which are frequently suggested for visitors interested in culture and architecture.
What are the best foods to try in Waukesha?
Classic Wisconsin cheese curds, locally crafted sausages, and Friday fish fry are frequently suggested. You will also find locally roasted coffee and a variety of baked goods at independent cafes and markets.
What should I bring for a trip to Waukesha?
Pack layers to stay comfortable through variable temperatures, especially between late fall and early spring when it can be chilly. Include waterproof shoes or boots and a rain jacket, as the area experiences periodic rainfall year-round. Outdoor gear is useful for exploring parks or trails around the city.
What is the nightlife in Waukesha like?
Waukesha has a welcoming downtown with live music venues, local breweries, and casual lounges. Evenings are often centered around community gathering spots and seasonal events, creating a relaxed, locally rooted vibe.
What are the most popular events or festivals in Waukesha?
Waukesha has a summer blues festival, weekly concerts in city parks during warmer months, and downtown art walks several times a year. Labor Day weekend and late summer often bring additional community celebrations and outdoor gatherings.
Are there family friendly vacation rentals in Waukesha?
Many vacation rentals in Waukesha accommodate families, especially in quiet residential areas and near parks. Spacious layouts and child-friendly amenities are often available to make family stays comfortable.
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- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Illinois Beach State Park
- Baird Center
- American Family Field
- Milwaukee County Zoo
- Milwaukee Public Museum
- Marquette University
- Riverside Theater
- Bradford Beach
- Pabst Mansion
- Discovery World
- Fiserv Forum
- Lake Geneva Public Library
- Gurnee Mills
- Holy Hill National Shrine of Mary
- Mitchell Park Horticultural Conservatory
- South Shore Park
- Betty Brinn Children's Museum
- Wisconsin State Fair Park
- Atwater Park
- Lake Geneva Cruise Line
- Lake Geneva Ziplines & Adventures