
House vacation rentals in Oconomowoc
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Top-rated house rentals in Oconomowoc
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Oconomowoc house rentals
House rentals with a pool

The Gem of Brewers Hill w/hot tub & seasonal pool
Excellent location and plenty of beds and bathrooms.

Cute and cozy 2 bedroom house perfectly located!
Our first time in Delafield and loved it!! Adorable little lake town with so many cute restaurants, coffee shop and ice cream just a short walk away. Elizabeth's home was exactly what we needed for a month long mother/daughter stay while attending treatment in the area. Meticulously clean at check-in and decorated so cute with finest attention to detail! So warm and cozy providing a perfect sanctuary. Elizabeth was flexible and responsive in all communication prior to and during our stay, and quickly addressed an Internet hiccup, ensuring the issue was resolved for us. Can't wait to return and highly recommend Elizabeth and this adorable gem of a home!!

Cozy cabin getaway near Lake Como and Lake Geneva
Sasha’s place was even better than expected. We all felt at home and it was very relaxing. We had plenty of room to accommodate all of the guests.

Abbey Springs Home! Hot Tub + Golf Cart
A wonderful home that was well appointed, clean & a great location! We hosted Easter here with my adult Kids and grandson. We all enjoyed the beautiful surroundings and all the wildlife-many deer and even a coyote! So much room and a great layout for us to enjoy the home together!

Newly Updated Modern Lake Condo
Loved this house! It was in a great location, a few mins away from town, walking distance to Lake Como and super easy to find and navigate. Everyone had a great time. Only drawback was a tiny kitchen for multiple people but the rest of the living areas were great!

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
We had a great stay at Steven’s lake condo! The place was exactly as described and had everything we needed. Steven was a great host and provided a very helpful guide ahead of time with information about check-in, the condo, and the surrounding area. We would definitely stay here again!

Oasis on Oak | Private In-Ground Pool | Hot Tub
House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!

Nestled in the Southern Kettle Moraine Forest
Jarvis and Chris are the kind of hosts who go above and beyond. We arrived after a chaotic day and were instantly welcomed with warmth, a surprise graduation cake and wine, and the peaceful reset we didn’t know we needed. The property is absolutely stunning—pictures do not do it justice. The trails are beautiful and serene, and the animals are the sweetest, most well-loved crew. You can feel how much care and heart goes into every part of this place. They also provided the best recommendations for dinners, hikes, and activities! If you’re thinking about booking—do it. You will not regret it. This place is a true Wisconsin gem. The love, care, and intention poured into it is obvious. We’re so grateful for this experience and already can’t wait to come back!
Weekly house rentals

The Yellow Door Guest House-Lower
very cool mid-century decor and filled with everything you might possibly need during your stay. the host was very responsive to messages. I was attending a wedding at Wildwood Cottage and this was an excellent lodging option for me. definitely would recommend to anyone staying in the area who appreciates a vintage vibe.

Blue House in the Pines
We had an amazing girls weekend, the house was exactly as described. So adorable, so many games to play and we felt amazing after a hot tub!

The Orchard House
This is one of the most aesthetically gorgeous, peaceful and unique Airbnb experiences I've enjoyed. What an absolutely lovely sanctuary of light, simplicity, and calm refuge just 30 minutes drive through rolling farmland, woods and wetlands from downtown Madison and the UW campus. The indoor fireplace and hot tub are such fabulous highlights! I loved every aspect of the orchard house including Josh's proactive tips and quick responses to a couple of minor questions I had. This was a really lovely place to spend a long weekend. I will be back and have already told all my friends about it. Bravo!

Bougie by the Beach
Jen was absolutely fantastic getting back to me with the information or answers to my questions. Honestly the pictures in the Airbnb app. do not do this place Justice. The detail that Jen has taken to make it comfortable and beautiful, amazing.

Pewaukee Lake Home steps from water & restaurants!
The house was super cute and cozy! It had two bedrooms, one bathroom, and an extra space in the basement. The kitchen was spacious, and it was perfect for three people to stay comfortably for a week. We really enjoyed our time here!

Watertown Family Retreat
Great host, house and experience. We were in town for a softball tourney, and the location was perfect. The house had everything we needed and more, like fresh strawberries from the garden. We'd stay again. Thank you!

Auburn Place: Cozy 3BR Home in Wauwatosa
Nice property with off street parking, close to everything you want to do in Milwaukee. *Almost* walking distance to watch a Brewers game (2.5 miles). Great grocery stores and restaurants nearby - some within walking distance. Check in earlier than most properties - and check out instructions were easy and reasonable. The hosts communicate well and any questions or concerns I had were answered promptly. Tosa is a quiet, safe, family suburb. This is a good option if your plans bring you to Milwaukee.

A-Frame in forest on bike trail!
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!
Private house rentals

Convenient, NFL Draft,Holy Hill, Golf, Skiing
A lovely place in the heart of Hartford. It was perfect for our visit to the Womens Open Golf at Erin Hills. Lots of good recommendations from Jennifer. We particularly liked Brewed Omen and MJ Market. The house was very clean and the kitchen had everything we needed. The golf backboard welcome was also a lovely touch. Thank you

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee
Amanda and Troy’s place was a great little bungalow for our first trip to Milwaukee. It was quick and easy to get to the highway, yet far enough to be situated it a quiet little neighborhood. Amanda and Troy really thought of everything! We took their recommendation and enjoyed walking to Blue’s Egg Cafe & Bakery. Would recommend their place for your next trip!

Farmhouse "The Inn"
Beautiful and cozy historic location! We had a great time and Karen was a wonderful, responsive, and friendly host. Our group had a wonderful reunion there.

Relaxing Lake House Getaway on Phantom Lake
We had a great stay while visiting Wisconsin

The Pike Lake Cottage House
We had a family reunion and had family from Texas and Florida coming in. We rented the AirBB for 3 nights for overflow. The AirBB was convenient, extremely clean and the view of the lake was breathtaking. Our Family enjoyed their stay.

1891 Home - Steps to Downtown & Free Breakfast
We thoroughly enjoyed our stay. The house was super clean, spacious, and charming—I only wish we had had more time to enjoy the lovely porch and get out in the neighborhood. The kitchen had everything we needed to cook in, the beds were comfortable, and the baths updated with plenty of towels. There are a lot of nice touches for visitors— hooks in the entryway for jackets, a baby gate to keep the dogs downstairs, big table in the dining area, and a spacious mud-room for all of our bags and such. The house is on a nice residential street but close to town and shopping, and it was an easy drive to the events we were attending in Jefferson and Johnson Creek. We would definitely stay here again if we are in the area.

Tranquil Wellness Retreat with Lake Views and Gym
We really enjoyed our stay and definitely would return. The home was clean and we felt right at home. Our dogs loved the yard and the view overlooking the lake was beautiful. The home was just as described, and check-in was easy. Nathan was responsive and communicated well throughout our stay. I would recommend staying at Nathan's, he is a great host, and we were grateful for our time there.

Luxury Lake Home-Miles of Lake Views-Private Pier
it's a beautiful property right on the water. it's unfortunate how close it is to the bar across the street and the neighbors homes, but that's lake living, I suppose! this property is sensational, well maintained. superb kitchen. wildlife is amazing. enjoy!
Quick stats about house rentals in Oconomowoc
Total rentals
20 properties
Nightly prices starting at
G$10,457 GYD before taxes and fees
Total number of reviews
750 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Geneva National Resort & Club
- Lake Kegonsa State Park
- Bradford Beach
- Racine North Beach
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Henry Vilas Zoo
- Milwaukee Country Club
- West Bend Country Club
- Wisconsin State Capitol
- Springs Water Park
- Heiliger Huegel Ski Club
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Sunburst
- America's Action Territory
- Blue Mound Golf and Country Club