Holiday rentals in Oconomowoc Lake

4.94 out of 5 average rating, 78 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, 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, 325 reviews

Flat 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

Flat 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.

5 out of 5 average rating, 49 reviews

Chic Retreat w/ Fire Pit by Wedding Venues + Lakes

Discover the Iron Ore Retreat, a stylish getaway mere minutes from downtown Oconomowoc! Situated in a quiet neighborhood, our pet-friendly🐶retreat boasts a whimsical backyard, close proximity to nearby lakes, golf courses, and wedding venues. Whether you’re planning a family retreat or a wedding haven, our delightful space is sure to capture your heart! ✨Traveling with a larger group or your preferred dates taken? Browse our host profile for the details on other listings in the area!✨

4.85 out of 5 average rating, 75 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, 143 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!

4.97 out of 5 average rating, 156 reviews

Apartment 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.

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

Place to stay in Racine

4.86 out of 5 average rating, 719 reviews

Wisconsin Treehouse Getaway!

ArielRating, 5 stars6 days 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!

Holiday home in Oconomowoc

4.86 out of 5 average rating, 116 reviews

Scenic 4 Bedroom WI Lake Home - Newly Renovated!

DonRating, 5 stars2 weeks ago

We stayed there for our daughter's wedding so we're not able to enjoy all the amenities that were available. It was so peaceful walking on the pier in the morning watching all the wildlife. The water is so clear you see the fish swimming. Definitely would recommend.

5 out of 5 average rating, 10 reviews

Flat in Port Washington

Mariner's Point Carriage House

LindaRating, 5 stars4 days ago

Was traveling solo and found the Carriage house to be easy to find and get into thanks to Lori's instructions. The finishes (countertops, window blinds, shower) are so lovely. It's nice to be able to enjoy a place that doesn't look like every other boring AirBnB. The bed was comfortable and the neighborhood was so quiet and walkable. The book of instructions and recommendations was a great resource. I had a few hours to relax in between activities and had a fun, cozy time watching a movie, listening to the gentle rain outside and enjoying some homemade treats provided by the hosts. When the sun came out, the neighbors could be seen walking their dogs, gathering together at local spots, and enjoying the lake. I can't wait to come back in the Fall.

5 out of 5 average rating, 5 reviews

Okauchee Lake Home

JoshuaRating, 5 stars11 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 stars1 week 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.

Cabin in Oconomowoc

4.67 out of 5 average rating, 3 reviews

Okauchee Lake Vacation Rental w/ Boat Dock!

RickRating, 5 stars1 week ago

Lovely little cabin right on the lake. A number of very good restaurants / bars within walking distance. It was a perfect place for our weekend getaway. Only complaint is that a more specific address is needed to find the place. We figured it out after a bit, but was quite confusing at first.

4.98 out of 5 average rating, 50 reviews

Home in Palmyra

A-Frame in forest on bike trail!

JaneRating, 5 stars2 weeks ago

Really a special place. It felt as though I was 100 miles away from civilization. Very quiet and peaceful. Lots and lots of migrating songbirds. 😍 The fenced yard was a real plus for me - traveling with two large dogs. Everything was super easy and very comfortable. Would definitely recommend!