Holiday houses in Oconomowoc

4.87 out of 5 average rating, 445 reviews

Home in Hubertus

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.

4.99 out of 5 average rating, 140 reviews

Home in Delafield

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.

4.91 out of 5 average rating, 118 reviews

Cabin in Oconomowoc

Beautiful Oconomowoc Log Home on 5.7 acres

Beautiful fully furnished non smoking Cabin 5.7 acres wooded lot in Ashippun, 6mls/Erin hills, 2mls/deer track, 8mls lac labelle golf course wedding venue Great room: 1couch & 1chair,natural fireplace 2 full bathrooms,4 bedrooms & 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

4.92 out of 5 average rating, 169 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!

4.95 out of 5 average rating, 327 reviews

Apartment in Bay View

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

4.95 out of 5 average rating, 139 reviews

Cottage in Hartland

Cozy cottage in the heart of Lake Country

Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

4.97 out of 5 average rating, 248 reviews

Apartment in Watertown

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

4.92 out of 5 average rating, 157 reviews

Townhouse in Waukesha

Cozy 2BR charm | Big Yard, Fire pit, Replenishing!

Cozy gem sleeps up to 5. Renovated Interiors w/ large balcony overlooking serene yard. Enjoy an eastern sunrise during your morning coffee, or a starry night next to the warmth of a fire. 1 mile from 94 - 20 minutes from Milwaukee. Fully stocked kitchenette. Gas burning stove/oven, microwave, coffee maker, full size fridge/freezer, in unit washer/dryer, wifi, smart tv, wireless printer, private large balcony w/ heater for cooler nights. Perfect space for a couple or traveling profesional.

4.96 out of 5 average rating, 291 reviews

Guest suite in Sussex

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

4.97 out of 5 average rating, 156 reviews

Condo in Lake Geneva

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

4.95 out of 5 average rating, 338 reviews

Cabin in Whitewater

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

Guest suite in Helenville

4.95 out of 5 average rating, 366 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.

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Other great holiday rentals in Oconomowoc

5 out of 5 average rating, 5 reviews

Apartment in Oconomowoc

Stylish 1BR Downtown Oconomowoc

CameronRating, 5 stars5 months ago

Spacious one-bedroom accommodation in the centre of Oconomowoc; well equipped and I didn't feel it was lacking anything. The pull down bed in the living adds even more flexibility if there's an extra person or two. The apartment is situated on the main street and is on the doorstep of shops, restaurants, cafes and bars. A little noise can be heard on the weekend evenings but nothing over the top, and pretty quiet the rest of the time. Communication for the most part was great, though did not have any direct contact with the host themselves, rather one the co-hosts, Feliccia, who was prompt in responding to any queries I had. Would definitely stay here again.

4.85 out of 5 average rating, 75 reviews

Oconomowoc Downtown River View

ShoshanaRating, 5 stars3 weeks ago

I was in Oconomonowoc for a conference, so had too little time to spend in Danielle's comfy home. I loved the time I did spend there! Especially comfortable beds, and I also appreciated having beautiful dishes to use. Thanks for a wonderful stay!

4.97 out of 5 average rating, 87 reviews

Home in Nashotah

Okauchee Lakefront Cabin Escape

BenjaminRating, 5 stars5 days ago

This is an amazing spot with a great view! Aaron's home felt so cozy. Very comfy and unique. The jukebox was a hit! Thanks Aaron!

4.94 out of 5 average rating, 78 reviews

Home in Nashotah

Beautiful home on Okauchee Lake, WI

DonRating, 5 stars1 week ago

Lovely house on the lake, as advertised. House was tastefully furnished and everything worked. Good restaurants nearby, but a special shout out to Smoke on the Water BBQ. It was in Cathy's recommendations, but we ate there a lot. We hope to stay there again next time we are in the area!

4.95 out of 5 average rating, 22 reviews

The Paddle House

ChristineRating, 5 stars5 months ago

We had such a wonderful Christmas at The Paddle House! The house was beautiful and Maria even had a Christmas tree set up for us! The view of the lake out of the huge living room window was amazing especially as it snowed! I would definitely recommend this property to anyone looking for a cozy oconomowoc getaway!

4.98 out of 5 average rating, 53 reviews

Home in Okauchee Lake

Cheerful, open space, and relaxing 1 bedroom home.

MarcoRating, 5 stars4 weeks ago

Exciting stayng in a wonderful Place. Okochee Is a stunning Little Town on the lake where you can find relax, peace and beautiful panorama. In the house of Kathy, Everything Is studied and smart. We Hope to come back to this Amazing accomodatiion. Thank you tò Kathy and Jacky .

5 out of 5 average rating, 49 reviews

Chic Retreat w/ Fire Pit by Wedding Venues + Lakes

ChristopherRating, 5 stars6 days ago

My family and I had a wonderful weekend in this beautiful home. Everything was very clean and modern. Great location for the area and the host(s) were very welcoming and responsive. Would definitely stay again.