House vacation rentals in Oconomowoc

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Top-rated house rentals in Oconomowoc

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Top guest favorite
The modern farmhouse is viewed from a distance, showcasing its clean white exterior and well-maintained landscaping. A paved driveway leads to the entrance, flanked by neatly trimmed bushes and vibrant green grass, creating an inviting approach to the home.
Home in Delafield
4.99 out of 5 average rating, 148 reviews

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.

Guest favorite
The exterior of a charming house is showcased, featuring a welcoming front porch adorned with string lights. Lush greenery surrounds the home, with a flower garden displaying purple blooms. A pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Menomonee Falls
4.94 out of 5 average rating, 161 reviews

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.

Top guest favorite
A historic home features a multi-gabled roof and intricate architectural details. The exterior showcases a blend of light and dark hues, complemented by well-maintained landscaping and a spacious lawn. A charming porch wraps around the front, providing an inviting entrance with rocking chairs nestled on one side.
Home in Wales
4.94 out of 5 average rating, 191 reviews

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

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, 181 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 favorite
The cozy sitting area features a mix of patterned sofas and an armchair, with warm ambient lighting from two table lamps. Rich green walls create a comfortable environment, while a view into the dining area is visible through an open doorway, adding to the home's vintage charm.
Home in Watertown
4.93 out of 5 average rating, 178 reviews

Beautiful Victorian in Historic District

My Victorian home, "Belle Maison" (beautiful house), is waiting just for you. Newly restored, with 2 bedrooms, 2 baths - one with its original claw foot tub!- and a queen size sofa bed in the TV room. It is located in historic, downtown Watertown. Just a block from Main Street - with lots of shops and restaurants within walking distance - and the beautiful Rock River. The location is perfect - whether you're visiting Jefferson County or looking for a home base between Madison and Milwaukee.

Top guest favorite
A historic cottage is set amidst lush greenery, featuring a mix of stone and siding on the exterior. A gravel driveway leads to the entrance, surrounded by well-maintained landscaping and mature trees that provide a tranquil atmosphere.
Home in Mequon
4.98 out of 5 average rating, 132 reviews

Historic cottage with fireplace. Pets Welcome!

Step back in time and immerse yourself in the charm of our historic 3-bedroom cottage, part of the renowned Jahn Farmstead, proudly listed on the National Register of Historic Places. Built in the mid-19th century, this Greek Revival-style farmhouse offers a unique blend of historical elegance and modern comfort, ensuring a relaxing and memorable stay. Located 2 miles from the Mequon Public Market and 5 miles from Cedarburg. Pets are welcome and we have acres of land for you to explore!

Top guest favorite
A living area features a stone fireplace and large windows providing views of Lake Beulah. Comfortable seating surrounds a wooden coffee table. A dining table is visible, alongside decor elements that create a cozy ambiance. Natural light floods the space, enhancing the connection to the outdoors.
Home in East Troy
4.98 out of 5 average rating, 119 reviews

Lakeside Getaway

Relax with the whole family at this peaceful, home on Lake Beulah. With the gorgeous lake and surrounding nature, you will feel you are hours up North, minus the long commute! Wake up and enjoy coffee on the deck. Bring your boat or grab a floaty and soak up the sun as you spend the day on the water. Wind down while you watch a stunning sunset from your own pier. Enjoy a show at the nearby Alpine Valley. Countless memories are just waiting to be made. Come play hard and relax even harder

Guest favorite
Two Adirondack chairs are positioned on a grassy area overlooking Lake Koshkongong. The bright blue sky complements the sunlight reflecting off the water, creating a serene waterfront setting.
Home in Edgerton
4.94 out of 5 average rating, 326 reviews

Vast Lake Koshkonong Views from Pier, Deck, & Home

Our 2 Bedroom, 1 Bathroom House is located directly on the shores of Lake Koshkongong. The back deck overlooks thousands of acres of lake with endless lake views. Just steps off the deck, one can enjoy the grassy landscape leading to the lakeside fire-pit. Then continue out onto the end of the 140 foot top notch pier. The pier (seasonally of course) includes a bench on the end and stairs into the water so that you can take a refreshing swim on our sandy bottom shoreline.

Guest favorite
An indoor pool area is showcased, featuring a large, clear pool with a projector screen positioned above. Natural stone walls and wood beams enhance the space, complemented by soft lighting. Large windows allow natural light to brighten the inviting environment.
Home in Sussex
4.89 out of 5 average rating, 123 reviews

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.

Top guest favorite
This log cabin is surrounded by greenery, showcasing natural stone accents and wooden details. A spacious deck features multiple hanging flower baskets, and stairs lead up to the entryway. The gently sloping driveway is lined with mulch and provides access to the cabin entrance.
Home in Dousman
4.97 out of 5 average rating, 175 reviews

Meracle Acres

Secluded among 50 acres of dense forest, stunning walking trails, wildlife and natural ponds, this one-of-a-kind log cabin is the perfect place to unplug and unwind. Whatever you’re looking for, you can find it all in this beautiful and tranquil getaway. Weekenders can enjoy hiking and exploring the gorgeous nature trails. The log cabin features a custom made bar, vaulted ceilings, a sauna room and outdoor hot tub with gorgeous views of the wildlife that surrounds.

Guest favorite
A charming two-story family home is seen through vibrant autumn foliage, showcasing yellow and orange leaves. A white wooden fence borders the property, with fallen leaves scattered across the lawn. The house features an upper balcony and large windows welcoming natural light.
Home in Oconomowoc
4.83 out of 5 average rating, 166 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 Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.

Top guest favorite
A spacious dining area features a wooden table surrounded by six chairs, complemented by an archway leading to a cozy living room. Natural light filters through large windows, illuminating the elegant combination of exposed brick and light-toned walls.
Home in Wauwatosa
4.97 out of 5 average rating, 127 reviews

Historic on The Avenue

Entire Home- 3 bedrooms This beautiful historic home is centrally located in the heart of Wauwatosa! Steps from the quaint village with restaurants, bars, coffee shops and boutiques! This property marries old world charm with modern amenities. Less than 15 minutes via freeway to downtown Milwaukee, the lakefront, Marquette University, less than 10 minutes to American Family Field, 5 minutes to the Milwaukee Zoo and Froedtert/Children's hospital.

Popular amenities for Oconomowoc house rentals

Quick stats about house rentals in Oconomowoc

  • Total vacation rentals

    Explore 20 vacation rentals in Oconomowoc

  • Nightly prices starting at

    Oconomowoc vacation rentals start at G$12,518 GYD per night before taxes and fees

  • Verified guest reviews

    Over 800 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Oconomowoc vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Oconomowoc rentals

  • 5 Average rating

    Oconomowoc stays are highly rated by guests—averaging 5 out of 5!

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