Holiday rentals in Oconomowoc

4.87 out of 5 average rating, 446 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.

4.91 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, 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.).

4.97 out of 5 average rating, 249 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.

4.93 out of 5 average rating, 164 reviews

Home in Watertown

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.

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.

4.94 out of 5 average rating, 305 reviews

Home in Edgerton

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.

4.99 out of 5 average rating, 142 reviews

Guest suite in Sussex

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

4.95 out of 5 average rating, 339 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.

4.95 out of 5 average rating, 404 reviews

Flat in Elkhorn

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

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Other great holiday rentals in Oconomowoc

4.85 out of 5 average rating, 75 reviews

Oconomowoc Downtown River View

ShoshanaRating, 5 stars4 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!

4.99 out of 5 average rating, 80 reviews

Flat in Oconomowoc

Stylish Historic Upper+King Bed/ Walk to Downtown

JanaRating, 5 stars3 days ago

The Blue Belle was perfect for our family of four adults during a wedding we attended in the area. There are two lakes and a cool upscale town area that's super walkable from the house. You'll find many restaurants, coffee shops and huge homes there plus a big friendly farmer's market Saturday mornings. Jason and Melissa were so easy to communicate and even checked in with us on the second day to make sure we had all we needed. I would stay here again!

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Cottage in Pewaukee

5 out of 5 average rating, 12 reviews

Lakeside Pewaukee Cottage

LaurelRating, 5 stars8 months ago

We were impressed by the cleanliness and open feeling of the place. It was a little smaller than we expected and had very limited seating but fit our group of 3 ok. I can’t imagine it being comfortable for a larger group though unless you’re only using the place to sleep! Overall it was a pleasant experience, beds were comfortable, kitchen well-appointed and the hot tub was nice, but we did feel that the price, once the cleaning fee was added on, was a little steep.

4.94 out of 5 average rating, 79 reviews

Home in Nashotah

Beautiful home on Okauchee Lake, WI

DonRating, 5 stars2 weeks 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 stars1 month 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, 63 reviews

Cottage in Delafield

Lake Country Guest Cottage

KateRating, 5 stars3 days ago

1 million stars! This cottage was absolutely a dream for my sister and me. The only downside was that we were not able to stay longer due to our own travel plans. Gorgeous property fabulous house, incredible location! Every single detail was thought of in this gorgeous cottage. Don't hesitate, just book it, you won't regret it.