
House holiday rentals in Oconomowoc
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Top-rated house rentals in Oconomowoc
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Holiday rentals for every style
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Popular amenities for house rentals in Oconomowoc
House rentals with a pool

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!

Luxurious BBQ and Pool House
We really enjoyed our stay at Chris's beautiful home. The location is private and quiet yet close to everything we needed. The amenities made it comfortable for our family to gather, dine and play. Thank you, Chris!

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
What a great place to relax! Best night sleep EVER. We were celebrating 30th anniversary of college graduation. Relaxed on patio after exploring Lake Geneva. Everything was spotless and excellent working order. Would definitely recommend.

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
The property was better than the description… Chris and Jarvis made us feel “like we were staying with friends” … The landscaping on the property is gorgeous and everywhere you went there would be something interesting to see … The animals on the property were wonderful for me, I left my “mini-farm” for this trip, it was very soothing to walk out and watch the animals as I was missing mine. The interior design was very tasteful, slightly different, but much better than the pictures. The extra’s - muffins, bread, bacon, fresh farm eggs, and an assortment of drinks - were above and beyond any Airbnb property I have stayed at!! I have to add … if you’re planning to stay for the Kettle Moraine 100 - this property is less than 10-minutes to the start/finish and within 25 minutes or less to all crew accessible aid stations! I really hope to have another opportunity to stay at this property and explore the surrounding areas.

Relaxing Summer Getaway near Lake Geneva w/ Pool
The house was a perfect fit for my family of 8. The amenities were great and Nicolet provided excellent communication.
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!

Bass & Sparrow - Spa Retreat on the MKE River
You would have no idea this place is in Milwaukee. It truly felt so secluded, like you were hours away from downtown. The hot tub, sauna, river right there…might has well been at a resort. Truly one of the most memorable weekends and we can’t wait to reserve another stay with Brad!

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.

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!

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

Cozy 3BR Ranch Home Away From Home
This is a lovely home! There is a sliding glass door, leading to a deck in a beautiful backyard. We really enjoyed eating our meals out there. The neighborhood is quiet, super clean, feels very safe—great for walks! Zelda is wonderful to work with. Our stay went off without a hitch!

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.

The Gatsby Getaway- a Charming Lakeside Retreat
Beautiful property with a lot of activities to keep the family busy. The sunsets over the lake were priceless. Doug purchased marshmallows roasters for us to use over the fire pit. Plenty of outdoor seating on the huge patio. The beds were amazing to sleep on. There was plenty of wild life to see and even had a groundhog that made appearances almost every day. Great place to relax and looking forward to staying there again.

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!

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!

Beautiful Lake Views While Lounging in the Hot Tub
Fantastic host, great spot, & very peaceful. Would recommend again! The house was gorgeous and the location was great!
Quick stats about house rentals in Oconomowoc
Total rentals
20 properties
Nightly prices starting at
$64 SGD 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
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Henry Vilas Zoo
- Harrington Beach State Park
- Milwaukee Country Club
- West Bend Country Club
- Wisconsin State Capitol
- Heiliger Huegel Ski Club
- Springs Water Park
- Discovery World
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Sunburst
- America's Action Territory
- Blue Mound Golf and Country Club