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Holiday houses in Oconomowoc

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Top-rated holiday rentals in Oconomowoc

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

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Top Guest favourite
Yurt in Cambridge
4.98 out of 5 average rating, 265 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 favourite
The cabin is set within a wooded area, featuring a welcoming front porch bordered by small shrubs and decorative plants. Natural materials are used in the construction, and the structure is highlighted by several windows and a sloping roof. Soft evening light creates a serene atmosphere.
Cabin in Oconomowoc
4.91 out of 5 average rating, 128 reviews

Beautiful Oconomowoc Log Home on 5.7 acres

Beautiful fully furnished non smoking Cabin 5.7 acres wooded lot in Ashippun, 6mls/Erin hills, forge golf crse1mls, 2mls/deer track, 8mls lac labelle golf/wedding Great rm: 1couch & 1chair,stone fireplace 2 full bathrms,4 bedrms & 3 floors:upstairs, grnd,basement; recrm, kitchenette, bdrm , 2 couches, pool table. Balcony Office/futon couch, pullout leather couch,1 bed Mastr closet,2 pullout single matrices in bsmnt, Swing set,sandbox, tree house, 2 fire pits, Back deck,grill, patio furniture

Guest favourite
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
4.93 out of 5 average rating, 192 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!

Top Guest favourite
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, 118 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 favourite
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, 113 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, 814 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 favourite
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, 125 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.

Guest favourite
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.
Holiday 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 favourite
Home in Oconomowoc
5 out of 5 average rating, 38 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 favourite
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.

Guest favourite
A log cabin sits perched on a grassy embankment, framed by trees. The exterior features large windows and a spacious deck with steps leading down to the water's edge. Two red chairs are placed near the shoreline, reflecting the cabin's warm colors on the water.
Home in Nashotah
4.95 out of 5 average rating, 133 reviews

Okauchee Lakefront Cabin Escape

The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.

Top Guest favourite
The spacious loft features a modern open layout, with a kitchen area showcasing white cabinetry and a large granite countertop. Natural light floods the space through multiple windows, highlighting a cozy seating area beside a fireplace and a unique handcrafted couch that doubles as a bed.
Guest suite in Helenville
4.95 out of 5 average rating, 381 reviews

Chic Loft Surrounded by Nature

This charming shabby chic loft sits in the heart of the country between Madison and Milwaukee. The Lighthouse Farm is also a wedding/event venue (please inquire for more details) . A quiet relaxing environment, with lots of open space, natural sunlight and lush green landscape. Great for those looking to get away with easy access to metropolitan areas, lakes, rivers and hiking/biking trails.

Popular amenities for Oconomowoc holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Oconomowoc

Guest favourite
Home in Oconomowoc
4.83 out of 5 average rating, 23 reviews

Lakefront Retreat • Hot Tub • 4BR • Genesee Lake

Top Guest favourite
Home in Pewaukee
4.93 out of 5 average rating, 76 reviews

Luxe Spa Cabin: Hot Tub + Sauna + Fire

Top Guest favourite
Home in Burlington
4.95 out of 5 average rating, 39 reviews

Long Lake Retreat - Cottage in Burlington, WI

Top Guest favourite
Home in Oconomowoc
5 out of 5 average rating, 21 reviews

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

Top Guest favourite
Home in Oconomowoc
5 out of 5 average rating, 16 reviews

Private Hot Tub • Bright Home Near Downtown

Guest favourite
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
4.91 out of 5 average rating, 22 reviews

Lake Country Retreat| Shared Pier Access|Lake View

Top Guest favourite
A fire pit area is surrounded by several black Adirondack chairs, set on a grassy lawn dotted with yellow flowers. Tall trees and greenery provide a natural backdrop, while a bright blue sky with scattered clouds enhances the tranquil atmosphere.
Home in Delafield
5 out of 5 average rating, 34 reviews

Remodeled Home on Wooded Lake Nagawicka Channel

Guest favourite
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

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