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Vacation rentals in Oconomowoc

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Top-rated vacation rentals in Oconomowoc

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Yurt in Cambridge
4.98 out of 5 average rating, 270 reviews

YurtSimple

YurtSimple is where life slows down and people unplug. It’s forest bathing in nature. It’s getting away from it all to spend time with a partner, by oneself, and sometimes with pets. You’ll be driving past YurtCation (about 300 feet past YurtCation) to get to YurtSimple. YurtCation is 20’ in diameter and YurtSimple is 16’ in diameter. Wood and charcoal are provided. You may cook on the indoor wood stove top, or visit any number of great restaurants 2 miles away. You can even order pizza delivery

Top guest favorite
A historic Victorian home showcases intricate architectural details, featuring a turret and a welcoming front porch. The light blue exterior is complemented by vibrant red accents. Lush greenery surrounds the property, enhancing its inviting presence in a serene neighborhood.
Apartment in Oconomowoc
4.99 out of 5 average rating, 120 reviews

Charming Historic Upper | Walk to Downtown & Lakes

Stay in a piece of Oconomowoc history. Whether you're here for a lakeside wedding or a quiet retreat, The Blue Belle offers designer interiors and comfy beds our guests love all steps from downtown. This charming town offers the perfect blend of adventure and relaxation, with shops, restaurants, wedding venues & activities all within walking distance. Browse our host profile for additional listings if your preferred dates are unavailable, are traveling with a larger group or a furry friend.

Guest favorite
A two-story grey house with white trim is presented, featuring a welcoming front porch. The porch is furnished with four bright yellow chairs, providing a cheerful spot to relax. The entrance door is located on the left, and large windows brighten the facade.
Home in Oconomowoc
4.92 out of 5 average rating, 196 reviews

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!

Guest favorite
A charming home is set among lush greenery, showcasing large windows that allow plenty of natural light. A stone wall supports a decorative patio area with several outdoor chairs and potted plants, creating a serene outdoor space. Tall trees frame the scene.
Home in Nashotah
4.92 out of 5 average rating, 116 reviews

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.

Superhost
Place to stay in Racine
4.84 out of 5 average rating, 817 reviews

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. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Guest favorite
A two-story house features a blue exterior with large windows illuminated by natural light. Lush green shrubs flank the entrance, while a small seating area consisting of metal chairs is set on a well-maintained lawn. A concrete path leads to the front door.
Home in Oconomowoc
4.86 out of 5 average rating, 128 reviews

Oconomowoc Downtown River View

Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

Top guest favorite
A spacious living area showcases a dark gray sectional sofa adorned with yellow and patterned cushions. A coffee table sits at the center on a patterned area rug, while a wall-mounted television is mounted nearby. Natural light enters through windows with a neutral-colored wall in the background.
Home in Delafield
4.95 out of 5 average rating, 197 reviews

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.

Guest favorite
The exterior of the vacation home features a welcoming walkway leading to the entrance. A well-maintained lawn surrounds the house, and two white chairs are positioned on a small patio, offering a pleasant outdoor seating area. Lush greenery and landscaping enhance the setting.
Vacation home in Oconomowoc
4.87 out of 5 average rating, 171 reviews

Scenic 4 Bedroom WI Lake Home - Newly Renovated!

Located just 30 mins west of Milwaukee lies this fabulous vacation lake home featuring 4 bedrooms, 2 full baths and unbelievable views of the lake throughout the home. Many popular restaurants and bars nearby, including “The Hideaway” right next door. Full lake and pier access, great for fishing and swimming. Nearby boat rental also available. 2 queen, 2 twin, and 1 king size bed along with two couches. The home has been recently renovated and feels like new. Free parking available.

Top guest favorite
Tall sunflowers bloom vibrantly in a garden, displaying bright yellow and orange petals. A wooden gazebo with hanging lights stands in the background, surrounded by lush greenery. Soft sunlight filters through the trees, enhancing the serene outdoor setting.
Guest suite in Sussex
4.99 out of 5 average rating, 158 reviews

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.

Top guest favorite
The exterior of the classic A-frame cabin, featuring a striking red facade, is set against a backdrop of lush greenery. A wooden walkway leads to a seating area with two chairs. A deck is visible, providing an inviting space to relax outdoors.
Home in Palmyra
4.99 out of 5 average rating, 101 reviews

A-Frame in forest on bike trail!

Classic A-Frame, in the woods. Borders the Kettle Moraine State Forest on 3 sides. Exterior: 2 acres, fully-fenced and dog-friendly. Hop on the "Connector" mountain bike trail right out the backyard. Or take a hike on the nearby Ice Age trail, Bald Bluff, John Muir, Nordic, or snowmobile trails. Interior: 1,500 square feet, 2 levels, open concept main living area with loft ceiling, wood-burning fireplace, 2 arcade machines, outdoor firepit, frisbee golf stand, etc.

Top guest favorite
Home in Oconomowoc
5 out of 5 average rating, 44 reviews

Forest Bay Cottage

Lakefront Getaway on Okauchee Lake – Cozy Cottage with Stunning Views! Escape to the serene beauty of Okauchee Lake with this charming 2-bedroom, 1-bath cottage, in Wisconsin’s Lake Country. Whether you're seeking a quiet retreat or outdoor adventure, this vacation rental offers it all. Located just 30 minutes west of Milwaukee and 50 minutes from Madison, you’ll have easy access to some of the best lakeside activities in the area!

Guest favorite
Home in Oconomowoc
4.82 out of 5 average rating, 175 reviews

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Pabst farms, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open and 2025 US Women's Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison.

Popular amenities for Oconomowoc vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Oconomowoc

Top guest favorite
Home in Pewaukee
4.93 out of 5 average rating, 80 reviews

Luxe Spa Cabin: Hot Tub + Sauna + Fire

Guest favorite
Home in Oconomowoc
4.85 out of 5 average rating, 26 reviews

Lakefront Retreat • Hot Tub • 4BR • Genesee Lake

Top guest favorite
Home in Oconomowoc
5 out of 5 average rating, 24 reviews

4 BD/4 BA Home, Perfect for Weddings & Group Trips

Guest favorite
A serene outdoor seating area features two Adirondack chairs positioned on a paved patio, offering a clear view of Lake Nagawicka. Lush green grass surrounds the space, with trees and a peaceful shoreline framing the scene.
Home in Delafield
4.92 out of 5 average rating, 24 reviews

Lake Country Retreat| Shared Pier Access|Lake View

Guest favorite
The exterior of the cottage features warm wooden siding and a welcoming porch with hanging flower baskets. A well-maintained pathway leads to the entrance, surrounded by lush greenery and low stone borders, creating a charming and inviting facade.
Home in Oconomowoc
4.96 out of 5 average rating, 28 reviews

The Paddle House

Top guest favorite
The living area features high, exposed wooden beams and large windows that allow ample natural light. A central island offers workspace in the kitchen, while a cozy seating area consists of a white chair and a unique side table, contributing to the open layout.
Home in Okauchee Lake
4.99 out of 5 average rating, 77 reviews

Cheerful, open space, and relaxing 1 bedroom home.

Guest favorite
A charming home is set against a backdrop of trees and greenery, featuring a combination of stone and siding exteriors. A spacious driveway leads to a welcoming entrance, with outdoor seating visible on the porch, inviting relaxation in the serene natural surroundings.
Farm stay in Oconomowoc
4.81 out of 5 average rating, 27 reviews

Back in Time

Guest favorite
Home in Oconomowoc
4.91 out of 5 average rating, 23 reviews

Lake Country Haven

Frequently Asked Questions

  • What are the best places to stay in Oconomowoc?

    Stays near the lakes, in historic neighborhoods, or around downtown are often recommended for easy access to parks, walking paths, and local eateries. Accommodations in residential areas provide a comfortable, community-rooted experience.

  • What are the best things to do in Oconomowoc with kids?

    Families can enjoy playgrounds, splash pads, and public beaches, along with exploring parks and community recreation centers. Locally rooted events and nature programs are often recommended activities for children.

  • What are some of the best things to do in Oconomowoc?

    Explore the lakes around downtown, stroll through historic neighborhoods, and visit local parks. Oconomowoc frequently suggests waterfront activities, seasonal festivals, and shopping in locally owned stores.

  • How is the weather in Oconomowoc?

    Oconomowoc experiences cold winters around 17–36°F (-8–2°C) with occasional snow, while summers are mild and pleasant, averaging 65–82°F (18–28°C). Spring and fall bring varied temperatures and moderate rainfall, so it's helpful to pack layers.

  • When is the best time to visit Oconomowoc?

    Late spring through early fall is often recommended for milder temperatures and outdoor activities, with summer afternoons bringing comfortable warmth around 77–82°F (25–28°C). Winter appeals to those who enjoy quieter visits and snowy landscapes.

  • What are the best places to visit in Oconomowoc?

    Explore the lakeside parks, downtown shopping streets, and historic landmarks around Oconomowoc. Visitors frequently walk public beaches, tour distinctive neighborhoods, and attend art or music events.

  • What are some hiking trails in Oconomowoc?

    Oconomowoc has walking and biking trails in public parks, with paths winding around the lakes and green spaces. Nature lovers frequently explore forested stretches, gentle loops, and lakeside routes.

  • What are some family activities we can do in Oconomowoc?

    Families often enjoy lakeside picnics, playgrounds, and interactive programs at local community centers. Seasonal festivals, outdoor movie nights, and nature exploration are popular choices throughout the year.

  • What are some of the best day trip ideas from Oconomowoc?

    Explore nearby state parks for hiking, visit regional museums, or discover historic towns with local markets and cultural sites. Outdoor recreation and arts experiences in surrounding areas are frequently suggested for day trips.

  • Are there any pet friendly accommodations available in Oconomowoc?

    Many stays in Oconomowoc welcome pets, especially in neighborhoods near parks or lakes. Outdoor spaces and walking trails make it easier to travel with dogs or other companions.

  • What are some local tips for visiting Oconomowoc?

    Locals often suggest packing comfortable shoes for lakeside walks and exploring independent shops or restaurants for a taste of the area's distinct charm. Check community calendars for recurring events, and enjoy outdoor spaces in every season.

  • What is Oconomowoc known for?

    Oconomowoc is known for its scenic lakes, historic architecture, and vibrant community events. The city's tradition of arts, waterfront recreation, and family-friendly festivals makes it a frequently suggested destination in Wisconsin.

  • What are the best hidden gems to explore in Oconomowoc?

    Discover tucked-away gardens, small art galleries, and locally owned cafés around Oconomowoc's historic streets. Locals often suggest scenic spots along lesser-known lake paths and unique shops.

  • What are the best foods to try in Oconomowoc?

    Oconomowoc has locally crafted ice cream, Wisconsin-style pizza, and freshwater fish dishes. Visitors frequently try artisan bakery treats, farm-sourced cheeses, and seasonal produce from local markets.

  • What should I bring for a trip to Oconomowoc?

    Pack comfortable walking shoes, a reusable water bottle, and weather-appropriate layers. Depending on the season, a light jacket or waterproof gear is frequently suggested for outdoor activities.

  • What is the nightlife in Oconomowoc like?

    Oconomowoc has casual venues, local bars, and restaurants, with occasional live music and community events. The vibe is laid-back and social, often centered around downtown gathering spots.

  • What are the most popular events or festivals in Oconomowoc?

    Oconomowoc often celebrates summer with arts and music festivals, farmers markets, and community gatherings near the waterfront. Holiday parades, cultural events, and seasonal outdoor concerts are frequently suggested for visitors.

  • Are there family friendly vacation rentals in Oconomowoc?

    Oconomowoc has many family-friendly vacation rentals, especially around the lakes and in residential neighborhoods. These stays often include spacious layouts, outdoor access, and amenities for children.

Destinations to explore