Oconomowoc vacation rentals

We found 98 vacation rentals — enter your dates for availability

Discover a selection of 21 homes and other vacation rentals in Oconomowoc that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Oconomowoc

Showing deals for:Nov 14 - Nov 21

Image gallery for Adorable lake house retreat - steps from the lake and restaurants!

Living area
9.6 out of 10 rating
Exceptional
(5 reviews)

Adorable lake house retreat - steps from the lake and restaurants!

Pewaukee, WI

8% off
Price is $303
$2,119 for 7 nights
All fees included
Adorable lake house retreat - steps from the lake and restaurants!

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Find out more about Oconomowoc

Find out more about Oconomowoc

Why visit Oconomowoc

  1. Scenic Lakes: Enjoy breathtaking views and water activities at Oconomowoc's beautiful lakes, perfect for relaxation and outdoor fun.
  2. Charming Parks: Explore picturesque parks that offer serene spots for picnics, walks, and family outings.
  3. Cozy Cafes: Savor local flavors at inviting cafes that provide a warm atmosphere for visitors to unwind.
  4. Cultural Events: Experience vibrant fairgrounds and various family-friendly events that showcase the town's rich culture.
  5. Diverse Accommodations: Choose from a range of cozy vacation rentals, including charming cottages and private homes.

Popular types of accommodation in Oconomowoc

Planning a getaway to Oconomowoc? You're in for a treat! Discover the charm of this beautiful area with our range of vacation rentals, including private homes, cozy cottages, and stylish apartments. Whether you're searching for a spacious villa or a quaint cottage rental, Oconomowoc offers accommodations that cater to every traveler's needs. Dive into your vacation with confidence and find the perfect home away from home!

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy during their stay in Oconomowoc, ideal for families or groups.
  • Apartments: A popular option for couples or solo travelers, apartments offer convenience and a home-like atmosphere close to local attractions.
  • Cottages: Quaint and charming, cottages provide a cozy escape for those looking to relax in a picturesque setting.
  • Cabins: Perfect for outdoor enthusiasts, cabins offer a rustic experience surrounded by nature.
  • Condos: Offering amenities and easy access to the area, condos are a great choice for a comfortable stay.**

Top attractions in Oconomowoc

Oconomowoc, Wisconsin, is the perfect destination for outdoor enthusiasts and romantic getaways. Visitors can explore beautiful lakes, modern colleges, and vibrant fairgrounds, offering diverse cultural and family-friendly experiences. Whether you're seeking scenic views or fun activities, Oconomowoc has something for everyone. Don't miss out on the charm of this lovely town during your vacation!

  1. Fowler Lake Park: This urban park offers a serene escape with beautiful lake views, walking trails, and picnic spots. Perfect for families, it features playgrounds and open spaces, making it an ideal place for outdoor activities and relaxation.
  2. Oconomowoc Arts Center: A hub for culture, this arts center hosts various performances and art exhibitions. Enjoy the rich artistic atmosphere and engage with local artists in this vibrant community space.
  3. Holy Hill: Located 13 miles away, this stunning church is known for its breathtaking architecture and serene grounds. Visitors can explore the beautiful basilica and enjoy panoramic views from the observation tower.

Things to do recommended for couples

For a romantic getaway in Oconomowoc, visit Pewaukee Lake Beach for luxury vibes, enjoy a wine tasting at Two Brothers Wines for a perfect blend of entertainment and romance, or hit the slopes at Heiliger Huegel Ski Club for some adventurous fun together.

Things to do recommended for families

Your family will love the serene vibes at Lac La Belle, enjoy outdoor fun at Imagination Station playground, and experience thrilling adventures at Springs Water Park, located 12 miles from Oconomowoc. This charming town offers a fantastic blend of relaxation and excitement for everyone!

Things to do recommended for groups

Experience the beautiful Oconomowoc Golf Club for a day on the green, shop at the nearby Johnson Creek Premium Outlets for some retail therapy, and enjoy the scenic Maple Wayside Trailhead for an adventurous hike. These activities promise fun and memorable moments for your group!

What do I need to keep in mind when booking a vacation in Oconomowoc

If you're planning a trip with a group, your family, pets, or seeking extended stays, be sure to refine your search based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Oconomowoc with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Oconomowoc with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with finding age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oconomowoc: For many families, a vacation isn't truly fulfilled without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oconomowoc: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Oconomowoc

Oconomowoc, a charming waterfront town in Wisconsin, offers a delightful blend of outdoor adventures and serene scenery. Perfect for family-friendly getaways or romantic escapes, visitors can explore picturesque parks, cozy cafes, and beautiful lakes. Just a short drive away, nearby cities enhance the experience with vibrant atmospheres and friendly locals, making it an ideal destination for relaxation and enjoyment. Come discover the warm, inviting vibes that Oconomowoc and its surroundings have to offer!

  • New Berlin: Located 22 miles from Oconomowoc, New Berlin is a vibrant city that offers a delightful mix of outdoor activities, family-friendly attractions, and romantic settings. Visitors can enjoy a variety of experiences, from catching a live theater performance to attending thrilling music concerts. Golf enthusiasts will appreciate the local courses, while sports fans can cheer on their favorite teams at nearby stadiums. With beautiful lakes and well-maintained parks, New Berlin is an excellent destination for those looking to connect with nature and create lasting memories.
  • Brookfield: Situated 19 miles from Oconomowoc, Brookfield is a bustling city known for its family-oriented atmosphere and business-friendly environment. The city boasts a range of shopping options, from expansive shopping malls to charming local boutiques. Visitors can enjoy a day at the fairgrounds or attend events at conference venues. With its lively urban vibe, Brookfield is perfect for those looking to experience city life while still being close to recreational spaces, including sports facilities and stadiums that host exciting events throughout the year.
  • Waukesha: Just 15 miles from Oconomowoc, Waukesha is a charming city that offers a wonderful blend of outdoor activities, family fun, and romantic spots. Music lovers can attend concerts or theater performances, while education-focused attractions provide enriching experiences for all ages. The city is known for its picturesque lakes and parks, perfect for leisurely strolls or picnics. Waukesha's vibrant community events and local sporting events at the stadium create an inviting atmosphere, making it a great stop for visitors looking to explore the area.

Best time to go to Oconomowoc

If you're planning a trip to Oconomowoc, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January19.8°F (-6.8°C)No Rain (Dry)Mostly CloudyAverageHigh
February21.7°F (-5.7°C)No Rain (Dry)Mostly CloudyAverageAverage
March34.5°F (1.4°C)Light RainMostly CloudyAverageLow
April44.6°F (7.0°C)Light RainMostly CloudySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageLow
June66.7°F (19.3°C)Light RainMostly SunnySlightly HighHigh
July71.4°F (21.9°C)Light RainMostly SunnySlightly HighAverage
August69.8°F (21.0°C)Light RainMostly SunnyAverageAverage
September63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
October50.2°F (10.1°C)Light RainMostly SunnySlightly LowLow
November37.6°F (3.1°C)Light RainMostly SunnySlightly LowAverage
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowHigh

Booking with Vrbo is simple

Are you hoping to save on your next vacation? Being flexible with your travel dates can often lead to significant savings, as prices tend to vary. Additionally, opting for a longer stay can help you secure even better deals. To help you find the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to assist you in making the most of your travel experience!

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash™ on your entire reservation. Being the planner truly has its perks! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on qualifying bookings. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing itineraries, or keep track of your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To start exploring your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Friendly Oconomowoc will entice you

Experience the unique character of Oconomowoc with a stay in a vacation home rental. Well-liked for its cafes, shopping and sporting events, this city is both welcoming and relaxing. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Oconomowoc

Are you looking for attractions to see while you're in town? Venture out of your cozy vacation rental and check out everything that makes Oconomowoc a fun spot to vacation. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Erin Hills Golf Course (11 mi / 17.7 km)
  • Springs Water Park (12 mi / 19.4 km)
  • Holy Hill (12.5 mi / 20.2 km)
  • Kettle Moraine Ranch (16.8 mi / 27.1 km)
  • Little Switzerland (19.2 mi / 30.8 km)
  • Cabela's (19.5 mi / 31.3 km)

Exploring the natural landscape of Oconomowoc

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Oconomowoc is a great place to get out in nature. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Fowler Lake Park (0.4 mi / 0.7 km)
  • Lac La Belle (1.6 mi / 2.5 km)
  • Nagawaukee County Park and Beach (7.7 mi / 12.3 km)
  • Pewaukee Lake (10.1 mi / 16.2 km)
  • Pewaukee Lake Beach (12 mi / 19.3 km)
  • Riverside Park (12.3 mi / 19.8 km)

Transportation options to and around Oconomowoc

The nearest airport is in Waukesha, WI (UES-Waukesha County), located 14.1 mi (22.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to General Mitchell Intl. Airport (MKE), which is 32.2 mi (51.8 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Oconomowoc?
Prices for vacation rentals in Oconomowoc 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oconomowoc to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oconomowoc vacation house rentals?
You can find great discounts on house rentals in Oconomowoc on Vrbo, 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.
Where are the best areas for renting a beach house in Oconomowoc?
For renting a beach house in Oconomowoc, Wisconsin, consider the picturesque shores of Oconomowoc Lake, where you'll find a variety of vacation rentals that offer stunning lake views. Properties in this area typically come with amenities such as private docks, expansive decks for outdoor dining, and access to water sports equipment, making them ideal for families or groups seeking a lakeside getaway.

Another great option is around the nearby Lac La Belle, which features charming cottages and spacious homes, often equipped with modern kitchens, cozy living areas, and outdoor fire pits for evening relaxation by the water. This region is not only superb for swimming and fishing but also provides opportunities for hiking and exploring the scenic trails around the lake.

Additionally, the downtown Oconomowoc area offers convenient access to local shops and dining, enhancing the overall experience for travelers. Rentals here often encompass a blend of convenience and leisure, with close proximity to parks, playgrounds, and community events that highlight the vibrant local culture. Find your rental near the beach in Oconomowoc.
What is the most popular type of vacation rental accomodation in Oconomowoc?
In Oconomowoc, vacation houses are the most popular type of rental, with about 17 available throughout the area. These houses typically offer spacious living arrangements, multiple bedrooms, fully equipped kitchens, and outdoor spaces for relaxing and enjoying the scenic views of the nearby lakes. Additionally, there are several condos, apartments, and cottages that provide alternative options for travelers. Many of these rentals feature amenities such as swimming pools, fitness centers, and access to recreational activities, making Oconomowoc a versatile destination for both families and couples looking for a comfortable stay.
Are there any family house rentals in Oconomowoc?
In Oconomowoc, Wisconsin, families will find a variety of vacation rentals available—around 15 options to choose from. This charming area is known for its beautiful lakes and outdoor recreational activities, making it an excellent choice for families looking to enjoy nature together.

Many of the properties offer spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play or families can gather for barbecues. Visitors can expect amenities such as Wi-Fi, air conditioning, and laundry facilities to ensure a comfortable stay.

The locale is close to local parks and the scenic Oconomowoc Lake, great for swimming, fishing, and boating. Additionally, the nearby downtown area features shops and restaurants, providing plenty of opportunities for family outings. See all family-friendly rentals in Oconomowoc.
Can I rent a vacation home with a pool or hot tub in Oconomowoc?
In Oconomowoc, there are several vacation homes available for rent with pools and hot tubs, with around 13 options to consider. This charming city, located between lakes and surrounded by beautiful nature, offers a variety of rentals that cater to travelers seeking relaxation and recreation. Many of these properties come equipped with private pools, spacious outdoor areas, and hot tubs, providing a superb setting for families or groups looking to unwind after a day of exploring.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and outdoor lounges, ideal for enjoying the scenic views of the surrounding lakes and wooded areas. The neighborhood near Oconomowoc Lake is particularly appealing, offering proximity to beautiful waterfronts and opportunities for water activities. Find your rental in Oconomowoc with a pool or a hot tub.
Can I find long-stay vacation rentals in Oconomowoc?
A long-stay vacation rental in Oconomowoc is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Oconomowoc?
In Oconomowoc, there are several pet-friendly house rentals available, offering a variety of amenities to enhance your stay. Many of these vacation rentals feature spacious layouts with fully equipped kitchens, outdoor spaces for pets to roam, and cozy living areas ideal for relaxing after a day of exploring.

The area is known for its beautiful lakes, providing ample opportunities for outdoor activities such as hiking, boating, and fishing, which can be enjoyed with pets. Additionally, nearby parks like Oconomowoc Lake Park and Fowler Park have walking trails and open spaces, making them superb spots for pet owners to take their furry friends for a stroll. See all pet-friendly rentals in Oconomowoc.
Are there any remote work vacation rentals in Oconomowoc?
In Oconomowoc, Wisconsin, there are numerous remote work vacation rentals available, with around 32 options to choose from. This charming city, situated between Lake Oconomowoc and Lac La Belle, provides a serene environment ideal for working remotely while enjoying the beauty of nature. Many properties feature dedicated office spaces equipped with desks, ergonomic chairs, and reliable Wi-Fi, ensuring a productive work atmosphere. Additionally, travelers can expect amenities such as full kitchens for preparing meals, comfortable living areas for relaxation, and some rentals may even include outdoor spaces to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Oconomowoc vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oconomowoc with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Oconomowoc?
In Oconomowoc, popular vacation rental amenities include WiFi, kitchens, coffee and tea makers, onsite parking, and patios. Many rentals are designed to provide a comfortable stay, allowing guests to prepare their own meals and enjoy the outdoors.
When is the best time to visit Oconomowoc for a vacation rental?
July is the most popular time to visit Oconomowoc, offering visitors a vibrant summer atmosphere great for enjoying the great outdoors. The peak season spans from June to August, when families and adventure seekers flock to the area to bask in the warm sunshine and partake in water activities on the beautiful lakes.

During these summer months, you can expect temperatures to hover in the mid-70s to low 80s Fahrenheit, creating an ideal climate for hiking, boating, and picnicking by the water. The charming downtown area comes alive with events and festivals, making it a wonderful time for those seeking a lively vibe and plenty of entertainment options.

For those looking for a more budget-friendly experience, consider visiting in November. This month provides a unique opportunity to explore Oconomowoc's serene landscapes as the fall colors transition and the holiday season approaches.
How early should I book a Oconomowoc vacation rental?
Book your Oconomowoc vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oconomowoc?
In Oconomowoc, visitors can enjoy a variety of attractions centered around its beautiful lakes. The Oconomowoc Lake area offers picturesque views and opportunities for water activities such as boating and fishing. The city's Main Street is vibrant, featuring local shops, cafes, and restaurants that reflect the charm of the community.

For outdoor enthusiasts, the nearby Lapham Peak State Park provides trails for hiking and biking, along with scenic overlooks. In addition, the Oconomowoc Arts Center hosts cultural events and performances, enriching the local arts scene and providing entertainment options for visitors.
Can I change or cancel my Oconomowoc home rental booking on Vrbo?
To find Oconomowoc vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oconomowoc vacation rental prices shown on Vrbo?
Vrbo 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.