Holiday houses in Oconomowoc Lake

4.94 out of 5 average rating, 79 reviews

Home in Nashotah

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 large bonfire pit and yard for playing games by the lake. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. The Nashotah Park is down the block.

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.

4.92 out of 5 average rating, 170 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, 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.).

Cabin in Fontana-on-Geneva Lake

4.92 out of 5 average rating, 139 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

4.97 out of 5 average rating, 249 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.

4.86 out of 5 average rating, 76 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.

5 out of 5 average rating, 145 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Need a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your inspired getaway awaits!

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.

4.99 out of 5 average rating, 80 reviews

Apartment in Oconomowoc

Stylish Historic Upper+King Bed/ Walk to Downtown

Looking for a memorable Wisconsin vacation experience? The Blue Belle is in the heart of Lake Country in a small town where you’ll find both adventure and relaxation! Located on a main street that takes you right to shops, restaurants, activities and wedding venues. All within walking distance. ✨Traveling with a larger group, your preferred dates taken or traveling with a furry friend 🐶? Browse our host profile for the details on other listings in the area.

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 Lake

4.96 out of 5 average rating, 182 reviews

Private room in Nashotah

Lake Country Loft , Quiet & Clean.

LaurenRating, 5 stars1 week ago

Nice place to stay

Place to stay in Racine

4.86 out of 5 average rating, 720 reviews

Wisconsin Treehouse Getaway!

ArielRating, 5 stars1 week ago

Beautiful space and property. Had a great stay and made wonderful memories. Main thing I’d say to be aware of is it is connected to the hosts’ actual home so keep that in mind. While the space is private, it’s not isolated. You may interact or hear the hosts’ family along the way. It wasn’t a big deal for us, but something to think about if you’re not fond of or used to it. Overall, great stay and recommend!

Apartment in Port Washington

5 out of 5 average rating, 13 reviews

Mariner's Point Carriage House

KellyRating, 5 stars2 days ago

Beautiful, quaint, cozy carriage house. Location was perfect, recommendations were great, deck with gas fire pit was perfect to unwind. Clean space. Very responsive! Thanks for enhancing our weekend getaway!

5 out of 5 average rating, 3 reviews

Forest Bay Cottage

BrettRating, 5 stars5 days ago

Forest Bay Cottage was the perfect spot to stay for my bachelor party! The house and amenities were just what we needed. The location is great and you absolutely cannot beat the view of the lake. Cool mornings spent outside on the deck overlooking the lake was the perfect way to start each of our days. Recommend to anyone and everyone regardless of the occasion, but for a little weekend getaway on the lake or a golf trip!

5 out of 5 average rating, 5 reviews

Okauchee Lake Home

JoshuaRating, 5 stars12 months ago

Tim was an excellent host, he was readily available for anything we needed and was proactive in his communication, ensuring our stay was going well.. His location on the lake is perfect, easy access to hwy 16, quick walk or drive to “downtown” Okauchee Lake. If you want a peaceful lake vacation in Lake Country we would 100% recommend this place Thank you Tim for a great stay.

Cabin in Hubertus

4.87 out of 5 average rating, 130 reviews

Glacier Hills Rustic Cabin #8

AmyRating, 5 stars2 weeks ago

Beautiful location right next to Lake Friess. You can see the lake from front and back of house. Deck was outstanding for hanging out on. Beds comfortable enough. Right next to hiking trails around the park as well. The park people are super quick to respond as well and had no problem extending our checkout time a couple hours. Would recommend.

5 out of 5 average rating, 9 reviews

Home in Delafield

Remodeled Home on Wooded Lake Nagawicka Channel

HeatherRating, 5 stars3 days ago

This place hit all the nails on the head. This might be the first time I booked accommodations for 8 women, different ages, styles etc, and noone complained. Thank you