House vacation rentals in Oconomowoc

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Top-rated house rentals in Oconomowoc

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Guest favorite

Natural wood accents are featured throughout the entryway, highlighting a stone fireplace and a warmly lit chandelier. A decorative area rug provides contrast against the light wooden floor, while a cozy armchair invites relaxation near the staircase leading to the upper level.

Home in Lake Mills

4.95 out of 5 average rating, 215 reviews

The Treehouse

Welcome to the Treehouse. This is our home away from home—and hopefully yours too. We love coming to the treehouse just off clear Rock Lake. The Treehouse is a getaway, although there are neighbors, you feel as if you are nestled in a grove of trees. The house itself provides places where guests can linger, relax, sip a glass of wine or a cup of java or simply just be. One of my favorite features is the glass windows that wrap up around the ceiling so that it feels like the outside is coming in.

Guest favorite

The exterior of a two-story home is visible, featuring large windows and a pleasant outdoor deck with shaded seating. A pergola is positioned nearby, surrounded by greenery and a stone pathway leading into the yard.

Home in Hubertus

4.87 out of 5 average rating, 457 reviews

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

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, 144 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

An archway leads into a living area featuring a light green sectional sofa and a patterned area rug. Natural light enters through large windows, complemented by curtains. A lamp stands nearby, and a small cabinet is positioned against the wall, creating a welcoming seating space.

Home in Menomonee Falls

4.95 out of 5 average rating, 150 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.

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

4.93 out of 5 average rating, 176 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

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

4.94 out of 5 average rating, 172 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, 124 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!

Guest favorite

Home in Wales

4.95 out of 5 average rating, 129 reviews

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

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, 114 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

4.93 out of 5 average rating, 315 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

4.88 out of 5 average rating, 116 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.

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

4.82 out of 5 average rating, 162 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.