Oconomowoc vacation rentals

We found 102 vacation rentals — enter your dates for availability

Select from 23 homes, 12 aparthotels, and other vacation rentals in Oconomowoc to find one that's 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.

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Find out more about Oconomowoc

Why visit Oconomowoc

  • Outdoor Adventures: Oconomowoc is ideal for nature lovers, offering beautiful parks and serene lakes for recreational activities.
  • Charming Downtown: Explore the picturesque downtown Okauchee with its welcoming locals, unique shops, and delightful eateries.
  • Small-Town Atmosphere: Experience the relaxed vibe of Oconomowoc, perfect for romantic getaways and family vacations.
  • Variety of Accommodations: Choose from cozy cottages, private vacation homes, and convenient apartments tailored to your needs.
  • Community Spirit: Discover local attractions that showcase Oconomowoc's vibrant culture and welcoming community.

Popular types of accommodation in Oconomowoc

If you're exploring vacation rentals in Oconomowoc, you're in for a treat. Our most popular accommodations include houses, cozy cottages, and convenient apartments. Whether you're looking for homes for rent, furnished rentals, or monthly stays, we have options to suit your needs. Many properties also come equipped with laundry facilities, and you can choose from select hotels for added comfort. Your perfect getaway awaits.

  • Houses: The most sought-after rental option in Oconomowoc, perfect for families or groups seeking a home-like atmosphere.
  • Cottages: A charming choice for visitors, these cozy retreats offer a rustic feel and are ideal for a peaceful getaway.
  • Apartments: Convenient and versatile, apartments provide a comfortable base for exploring the area.
  • Cabins: Rustic cabins offer a unique experience, allowing guests to enjoy nature while still having modern comforts.
  • Condos: A popular choice for travelers, condos combine hotel-like amenities with the space of a home.**

Top attractions in and around Oconomowoc

Oconomowoc, Wisconsin, is a charming destination perfect for outdoor enthusiasts and those seeking a romantic getaway. With its beautiful parks, serene lakes, and local medical centers, visitors can enjoy a blend of culture, family experiences, and nature. Whether you're exploring scenic landscapes or indulging in leisurely strolls, Oconomowoc offers a delightful escape for travelers of all kinds.

  • Fowler Lake Park: A serene urban park in Oconomowoc, perfect for families and outdoor enthusiasts. Enjoy picturesque views of Fowler Lake, walking trails, and picnic areas that create a welcoming atmosphere for relaxation and recreation.
  • Oconomowoc Memorial Hospital: While primarily a medical center, it embodies a community spirit with family-friendly services and business-oriented facilities. It represents the town's commitment to health and wellness.
  • Holy Hill: Located 13 miles from Oconomowoc, this stunning church offers a unique cultural experience, featuring breathtaking architecture and tranquil grounds, ideal for reflection and appreciation of spiritual heritage.

Things to do recommended for couples

Planning a romantic getaway in Oconomowoc? Visit Pewaukee Lake Beach, a luxurious country club only 12 miles away. Enjoy serene views, relax on the beach, and create unforgettable memories together in a picturesque setting.

Things to do recommended for families

Families can explore the scenic trails at the Oconomowoc River Walk, enjoy a day at the beach at Fowler Lake Park, or visit the Oconomowoc Historical Museum for fascinating local history. Don't miss the interactive exhibits at the nearby Imagination Station for a fun learning experience.

Things to do recommended for groups

Explore the picturesque Oconomowoc Lake with a boat tour or gather your group for a fun-filled day at the Oconomowoc Arts Center. Enjoy local dining experiences at charming restaurants and take scenic walks along the lakeshore trails for a memorable outing.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip—whether you're traveling with a group, family, pets, or looking for extended stays—be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Oconomowoc with a group: Think about how many bedrooms you'll require and any additional features you might want, like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to Oconomowoc with young kids: Traveling with little ones can be tough. It’s important to prioritize their comfort and safety, along with amenities suitable for their age, like a private pool. Additionally, keeping in mind the closeness to family-friendly activities is a wise choice.
  • Taking your pets with you to Oconomowoc: For many families, a vacation wouldn't feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Oconomowoc: If you're searching for vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to refine your search.

Where to stay in and around Oconomowoc

Oconomowoc, Wisconsin, offers a charming blend of outdoor adventures and scenic views perfect for a romantic getaway or family-friendly vacation. Explore the picturesque downtown Okauchee, where friendly locals welcome you to enjoy local shops and eateries. Venture into Waukesha County's open spaces for recreation, and immerse yourself in the small-town atmosphere that makes Oconomowoc a relaxing retreat. Discover interesting places that highlight the community's charm and vibrant spirit during your visit.

  • Delafield: Located 6 miles from Oconomowoc, Delafield is a charming city known for its stunning natural beauty and vibrant outdoor scene. Visitors flock here for romantic getaways and picturesque scenery, making it a perfect destination for couples and nature lovers. Delafield boasts a variety of attractions, including a recreational area ideal for hiking and biking, a local theater offering artistic performances, and music concerts that fill the air with culture. Key landmarks include a scenic lake, a state-of-the-art sports facility, and lush parks, all contributing to an enriching travel experience.
  • Okauchee Lake: Nestled within the Oconomowoc area, Okauchee Lake is a delightful village that attracts visitors seeking outdoor adventures and serene landscapes. Known for its romantic ambiance, this destination features a beautiful lake surrounded by parks and recreational areas. Travelers can enjoy activities like golfing at scenic courses or relaxing in the urban parks that dot the village. The tranquil environment and lush greenery provide a perfect backdrop for leisurely strolls or picnics, making it an ideal spot for relaxation and enjoyment.
  • Oconomowoc Lake: Oconomowoc Lake, another picturesque village in the Oconomowoc vicinity, offers a blend of outdoor beauty and recreational opportunities. This charming area is popular among tourists for its scenic views and romantic atmosphere. Visitors can explore playgrounds, golf courses, and recreational areas that cater to both families and couples. The tranquil lakeside parks provide a perfect setting for relaxation and fun, with opportunities for water activities and leisurely walks. Overall, Oconomowoc Lake is a lovely escape for those looking to immerse themselves in nature.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.8°F (-6.8°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
February21.7°F (-5.7°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
March34.5°F (1.4°C)Light RainMostly CloudyAverageSlightly Low
April44.6°F (7.0°C)Light RainMostly CloudySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainMostly SunnySlightly HighSlightly High
July71.4°F (21.9°C)Light RainMostly SunnySlightly HighSlightly High
August69.8°F (21.0°C)Light RainMostly SunnyAverageSlightly High
September63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
October50.2°F (10.1°C)Light RainMostly SunnySlightly LowAverage
November37.6°F (3.1°C)Light RainMostly SunnySlightly LowAverage
December27.5°F (-2.5°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Are you interested in saving money on your upcoming trip? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your itineraries, or review and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Oconomowoc Golf Club (1.9 mi / 3 km)
  • Erin Hills Golf Course (11 mi / 17.7 km)
  • Springs Water Park (12 mi / 19.4 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)
  • Holy Hill (12.5 mi / 20.2 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

What is the best area to stay in Oconomowoc, Wisconsin, United States of America when booking a vacation rental?
When considering a vacation rental in Oconomowoc, Wisconsin, a popular area to stay is near the beautiful Lakeshore area. This picturesque neighborhood offers stunning views of the lake and easy access to outdoor activities such as boating, fishing, and hiking along scenic trails. You'll find a variety of charming rental properties here, with many providing a cozy, lakeside experience.

In addition to the natural beauty, Lakeshore is close to top attractions like the Oconomowoc Arts Center, which hosts various cultural events and performances, making it a great spot for art enthusiasts. Another point of interest is the nearby Oconomowoc Lake, superb for leisurely strolls or enjoying a picnic.
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, the area surrounding the beautiful Oconomowoc Lake is a prime choice. This area features a variety of vacation rentals that offer stunning views of the water and easy access to sandy shores. Properties along the lake often come with amenities such as private docks, outdoor decks, and spacious backyards great for barbecues and gatherings. Many homes also provide modern kitchens and comfortable living spaces, accommodating families or groups looking for a relaxing lakeside getaway.

The nearby city center offers additional attractions, including charming shops and local restaurants, ideal for travelers. Additionally, the Lake Country area features parks and walking trails, where visitors can enjoy nature and outdoor activities. Rentals near these parks often include features like fire pits and picnic areas, ideal for enjoying the serene surroundings. 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 18 available in the area. These properties often feature spacious layouts, multiple bedrooms, and amenities such as fully equipped kitchens and inviting living areas, making them ideal for families or groups. Additionally, there are several condos, apartments, and cottages that cater to travelers looking for a more compact living space. Many of these rentals are situated near scenic spots like Oconomowoc Lake and the charming downtown area, where visitors can enjoy local shops and restaurants.
Are there any family house rentals in Oconomowoc?
In Oconomowoc, Wisconsin, there are some available family-friendly house rentals, totaling around 16 options throughout the area. The locale is known for its beautiful lakes and parks, making it an ideal destination for families seeking outdoor adventures. Many of these homes offer spacious living areas, full kitchens for preparing meals together, and outdoor spaces where children can play and enjoy the fresh air.

Properties often feature amenities such as Wi-Fi, air conditioning, and sometimes even game rooms or private yards. Families can easily access local attractions like the Oconomowoc Lake and the nearby parks, where hiking trails, playgrounds, and picnic areas provide fun activities for everyone.
Can I rent a vacation home with a pool or hot tub in Oconomowoc?
In Oconomowoc, there are several vacation homes available for rent that feature pools and hot tubs, with around 15 options to choose from. This beautiful city, situated between the scenic lakes of the area, offers a variety of properties in neighborhoods such as the charming downtown area and along the shores of Lake Oconomowoc.

Travelers can expect a range of amenities in these rentals, including private pools, relaxing hot tubs, spacious outdoor decks, and well-equipped kitchens, ideal for both family gatherings and entertaining.
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 welcoming environment for both travelers and their furry companions. Many of these vacation homes come equipped with modern amenities, including spacious living areas, fully equipped kitchens, and outdoor spaces such as patios or yards. This makes them ideal for families or groups looking to enjoy their stay while accommodating pets comfortably.

The area around Oconomowoc is known for its beautiful lakes and parks, providing ample opportunities for outdoor activities with pets. Nearby parks often feature walking trails and scenic views, great for leisurely strolls or energetic playtime with dogs. The charming downtown area is also accessible, with local shops and cafes that may welcome pets, enhancing the overall experience for visitors traveling with their four-legged friends. See all pet-friendly rentals in Oconomowoc.
Are there any remote work vacation rentals in Oconomowoc?
In Oconomowoc, Wisconsin, there are several vacation rentals suitable for remote work, with around 35 options available. Many of these properties come equipped with essential amenities for working from home, such as high-speed Wi-Fi and designated office spaces. Some rentals even offer free internet access, ensuring a reliable connection for video calls and other online tasks.

Travelers can expect comfortable living areas that allow for productivity, alongside additional features like spacious work desks and quiet environments. The scenic surroundings of Oconomowoc also provide a pleasant backdrop for breaks, with opportunities to explore local parks, lakes, and charming downtown shops. 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 onsite parking, which provides convenience for travelers with vehicles. Most rentals feature a kitchen, allowing guests to prepare their own meals, and many offer comfortable living spaces with a deck or patio for enjoying the outdoors. Fireplaces are also common, adding a cozy touch, especially during cooler months. Additionally, fitness facilities are available nearby, suiting those who wish to maintain their exercise routines while away.
When is the best time to visit Oconomowoc for a vacation rental?
The best time to visit Oconomowoc for a vacation rental is during the peak season from June to August, particularly in July, when the town comes alive with vibrant summer activities. This is an excellent choice for families and outdoor enthusiasts who appreciate warm weather and the chance to explore the beautiful lakes and parks in the area.

During these summer months, temperatures typically range from the mid-70s to the low 80s Fahrenheit, creating ideal conditions for boating, fishing, and hiking. Visitors can also enjoy local festivals and events, which add to the lively option and provide a great opportunity to connect with the community.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, superb for those who enjoy a peaceful retreat while still taking in the serene fall scenery. The crisp air and colorful leaves create a picturesque backdrop for leisurely strolls around the lakes.

Ultimately, your ideal time to visit Oconomowoc depends on whether you prefer the bustling energy of summer or the tranquil charm of the fall.
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, Wisconsin, United States of America?
In Oconomowoc, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque Oconomowoc Lake is a focal point, offering opportunities for boating, fishing, and scenic walks along the shoreline. The nearby Fowler Lake Park features walking trails, picnic areas, and a playground, making it a great spot for families and outdoor enthusiasts alike.

The downtown area is charming, with unique shops, cafes, and restaurants that reflect the town's small-town charm. The Oconomowoc Arts Center often hosts performances and events, providing a cultural hub for the community. For those interested in history, the Oconomowoc Historical Museum offers insights into the local heritage and is a great educational stop.

Additionally, the surrounding areas have several parks and nature reserves, such as the nearby Lapham Peak State Park, which provides hiking trails and stunning views, especially from its observation tower.
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 cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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