
Vacation rentals in Pewaukee
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Top-rated vacation rentals in Pewaukee
Guests agree: these stays are highly rated for location, cleanliness, and more.

Bark Lake, Entire Home, Private Lake Frontage 50ft
A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

Modern Lake Country Farmhouse in Delafield
Just a half mile outside downtown Delafield, this charming, modern farmhouse is clean, updated and well stocked. There's plenty of space to have a peaceful, relaxing stay. Easy access to golf, lakes (like Nagawicka and Upper & Lower Nemahbin), parks (like Lapham Peak State Park), hiking, biking and x-country skiing. Enjoy walking access to restaurants and shops in Delafield. Just minutes off I-94 in Lake Country, conveniently located between Milwaukee and Madison. 30 minutes from Fiserv Forum.

Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Black Squirrel Farmhouse - (Downtown Oconomowoc)
Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Cozy cottage in the heart of Lake Country
Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

Beautiful Bay View MKE Flat - w/parking!
This is a bright, sunny apartment on the upper level of a sweet little 1870's "Polish Flat" in the heart of Bay View, one of the city's most desirable neighborhoods! We are just steps away from some of Milwaukee's best restaurants, bars, taprooms, boutiques and coffee shops. The space features an efficiency kitchenette, living room, beautiful bedroom and renovated bathroom with walk-in shower! Close to East Side, Walker’s Point, Historic Third Ward, Summerfest, Mitchell Park and the airport.

Beautiful home on Okauchee Lake, WI
I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

Wisconsin Treehouse Getaway!
Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. And if we're home, a complimentary Chai for you! Come, make lifelong memories at Racine's Best Kept Secret!

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.

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.

Pet-Friendly | Large Yard | Fire pit | Sleeps 5
Wake up to the sunrise over a peaceful backyard and enjoy your favorite blend on your private balcony. Evenings are perfect by the fire pit under a starry sky. This renovated home has gas stove/oven, microwave, coffee maker, full-size fridge/freezer, in-unit washer & dryer, smart TV, and Wi-Fi - ideal for couples, small families, or traveling professionals. Only 1 mile from I-94 and 20 minutes from Milwaukee, blending quiet comfort with city convenience.
Popular amenities for Pewaukee vacation rentals
Other great vacation rentals in Pewaukee

Blue Chair Retreat -New Lakefront Home

Designer Home with Lake Views & Upper Balcony

Lakeside Pewaukee Cottage

Pewaukee Serenity Cottage: Whimisical by the Lake

Forest Bay Cottage

Bougie by the Beach

South Shore Guesthouse

All Aboard: One of a Kind Voyage on Pewaukee Lake!
When is the best time to visit Pewaukee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $238 CAD | $216 CAD | $210 CAD | $209 CAD | $294 CAD | $289 CAD | $290 CAD | $275 CAD | $245 CAD | $233 CAD | $231 CAD | $268 CAD |
| 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
How much does it cost to stay in house rentals in Pewaukee?
Experience the best of Pewaukee with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Pewaukee?
Yes! Work meets play with ease at over 10 house rentals in Pewaukee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Pewaukee?
Make yourself at home in Pewaukee by choosing from our most frequently booked neighborhoods. We have over 30 vacation rentals in Rocky Point, over 30 vacation rentals in Meadowbrook Heights, and over 30 vacation rentals in Springdale Estates.
Are there family-friendly house rentals in Pewaukee?
Pewaukee has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly house rentals in Pewaukee?
Four-legged friends are welcome in Pewaukee. Choose from more than 10 house rentals for guests traveling with pets.
Do house rentals in Pewaukee have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Pewaukee. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pewaukee have wifi?
Absolutely! We offer over 30 house rentals with wifi in Pewaukee. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Pewaukee?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about vacation rentals in Pewaukee

Total vacation rentals
Explore 50 vacation rentals in Pewaukee

Nightly prices starting at
Pewaukee vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 1,390 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Pewaukee vacation rentals include wifi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Pewaukee rentals

4.9 Average rating
Pewaukee stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Six Flags Great America
- Alpine Valley Resort
- Kohler-Andrae State Park
- Wilmot Mountain Ski Resort
- Erin Hills Golf Course
- Illinois Beach State Park
- Milwaukee County Zoo
- Milwaukee Public Museum
- Bradford Beach
- Baird Center
- Sunburst
- Discovery World
- Riverside Theater
- Marquette University
- Fiserv Forum
- Lake Park
- American Family Field
- Holy Hill National Shrine of Mary
- Little Switzerland Ski Area
- Lake Geneva Cruise Line
- Lake Geneva Public Library
- South Shore Park
- Betty Brinn Children's Museum
- Gurnee Mills




