House vacation rentals in Oconomowoc

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Top-rated house rentals in Oconomowoc

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Guest favorite

The exterior of the lakeside home is depicted, featuring a single-story structure with light-colored siding. A spacious green lawn surrounds the property, complemented by several trees. Outdoor seating arrangements can be seen, providing an inviting space for relaxation.

Home in Juneau

4.85 out of 5 average rating, 133 reviews

Take a Break at Lakeside Acres

Lakeside Acres; a 2-bedroom, 1 bath vacation rental home located on beautiful Lake Sinissippi. Open concept living area with furnished patio and private dock. This newly updated home provides the perfect summer getaway or winter retreat for family and friends. Whether you spend your days kayaking with the complimentary kayaks, exploring Horicon Marsh, or soaking up the sun on the dock, you're sure to have an unforgettable stay in this lakefront hideaway. Note: Docks are not in the lake Nov-Apr.

Guest favorite

A living area is observed, featuring a comfortable couch adorned with decorative pillows. A light-coloured coffee table sits in front, complemented by a patterned ottoman. A workspace with a small desk and dining area is visible in the background, surrounded by windows allowing natural light to enter.

Home in Hubertus

4.86 out of 5 average rating, 433 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 exterior of a gray house features a welcoming front porch with white railings. Symmetrical windows are bordered by tall evergreen shrubs, and a manicured lawn stretches out in front. The structure has a classic charm with a peaked roof and is surrounded by trees.

Home in Thiensville

5 out of 5 average rating, 181 reviews

Charming retreat-like 3BR in desirable northshore

Charming retreat-like 3BR in desirable northshore community walkable to coffee shops, restaurants, parks & the riverwalk…or a quick 23 minute ride to the front of the Fiserv Forum in downtown Milwaukee! Great for the weekend getaway, business trip or extended vacation. WIFI, well appointed kitchen, 2.5 bath, gas FP & front porch rocking chairs to watch the parade of dog walkers. Walk to (excellent) authentic Himalayan food at the Cheel or a glass of wine at Glaze while painting a new coffee mug!

Guest favorite

Home in Milwaukee

4.89 out of 5 average rating, 122 reviews

Good Land Home - Shorewood / Milwaukee, WI

From activities and attractions to fairs and festivals, Milwaukee, has something for everyone in your travel group! After each adventure-filled day, look forward to returning to this 3-bed, 1.5-bath upper duplex house featuring a fully equipped kitchen, bright living space, and comfortable accommodations for 6. There's a variety of things to do in Milw including award winning dining, pro Sports, Brewery tours, endless music festivals and more! Indoors or outdoors, the opportunities are endless!

Guest favorite

Home in Edgerton

4.92 out of 5 average rating, 118 reviews

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill

Gather at the White House: a stylish lake house with private pier, 4Br/2.5bath/beds for 15 people, fire pit, gas grill, huge yard, 2 wooded acres. Lake Koshkonong is one of WI’s largest, famous for its boat-up restaurants/bars, fishing, and water sports all accessible from our private pier. Located along 39/90hwy - 90 mins to Chicago/30 min to Madison. Perfect for entertaining: fully stocked, professionally cleaned, open floorplan, 3-story outdoor living, dining & patio, playroom & much more!

Top guest favorite

A vibrant game room displays colorful wall art and a geometric area rug. It features a comfortable couch, a sleek daybed, and a multi-game arcade station. Large windows provide ample natural light, and the garage door opens to the outdoor area, enhancing the space.

Home in Elkhorn

4.98 out of 5 average rating, 146 reviews

Red Lodge - Game Room, Hot Tub, Near Lake

Looking for a memorable Wisconsin vacation experience? The Red Lodge is the ideal blend of comfort and style. Super clean, fully stocked, with gorgeous outdoor green spaces and unique amenities, you'll love it here! Jeff - "The devil is in the details, and no detail is overlooked here." Kelsey - "We are obsessed! This is THE nicest Airbnb we've stayed in across the country.. There was something truly unique about each room." Alia - "Hands down the best Airbnb we have ever stayed in."

Guest favorite

A spacious living area is presented with a large, comfortable sectional sofa and an armchair. A wooden coffee table sits on an ornate area rug, and natural light filters through sheer curtains, highlighting the warm wooden floors and accent furniture.

Home in Bay View

4.96 out of 5 average rating, 140 reviews

Bright and Roomy Multi-Level Bay View Flat

Enjoy all that Bay View has to offer in centrally located Haas House! Bright, sunny, spacious upper flat with historic charm. Unique two level layout includes formal dining room, eat in kitchen and large sunny deck. Ring doorbell, 2 Smart TVs, large upper deck. Huge Master Suite includes living area, private bathroom, work space and Smart TV. Close to bars, restaurants, and Lake Michigan. 10 minutes to airport and downtown. Easy street parking. Perfect location for exploring Milwaukee.

Guest favorite

A modern kitchen is highlighted by vibrant green cabinetry and functional full-sized appliances. A wooden dining table is surrounded by gray upholstered chairs, creating an inviting space for meals. Shelving above the counters holds various kitchen essentials, enhancing the well-stocked atmosphere.

Home in West Allis

4.9 out of 5 average rating, 147 reviews

KING BED/Amazing Location/Free parking/Wi-Fi

Enjoy a fun and relaxing stay with family or friends in this stylish, cozy, and comfortable lower unit, which features: 2 bedrooms (1 king, 1 queen ) 1 bathroom Fully equipped kitchen with dining table and designated coffee bar Living room with a 65” smart TV (Netflix included) Home office space Free parking spot Located just a short drive (4 min) from I94, this home offers easy access to all the city's major attractions * the ideal base for exploring the best of Milwaukee

Superhost

A bright living area is filled with natural light from multiple windows adorned with bamboo shades. Comfortable seating includes two armchairs and a plush sofa, complemented by a simple coffee table and minimalist decor. A dining area is visible in the background.

Home in Racine

4.88 out of 5 average rating, 406 reviews

The July House: Lake Views & Old World Charm

You are invited to come enjoy the amazing lake views from this adorable 1920’s house! Our family used to live here, and we loved it way too much to sell it. The whole space has since been re-imagined for guests, including two full newly-renovated modern baths. Some interesting original features still remain, such as exposed Cream City brick and a wood burning fireplace. Lake view from living/sitting room and all bedrooms, and within walking distance to downtown food/shops.

Top guest favorite

The cottage features a charming facade with a combination of blue siding and stonework. Two sets of double doors are framed by large windows, allowing natural light to fill the entrance. Flower beds line the pathway leading to the front door, enhancing the welcoming appearance.

Home in Elkhorn

4.98 out of 5 average rating, 123 reviews

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

Top guest favorite

A spacious guest home is set against a backdrop of tall trees, positioned near a sandy beach. The exterior features a covered porch and two lounge chairs, inviting relaxation while enjoying the serene landscape.

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Guest favorite

The exterior of a two-story blue lakeside home is displayed, featuring large windows that allow for ample natural light. Adjoining the home, a well-maintained lawn is complemented by a fire pit area with light green Adirondack chairs, creating an inviting outdoor space.

Home in Beaver Dam

4.91 out of 5 average rating, 108 reviews

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.