House holiday rentals in Oconomowoc

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Oconomowoc

House rentals with a pool

Top guest favourite
Home in Delafield
4.95 out of 5 average rating, 40 reviews

Cute and cozy 2 bedroom house perfectly located!

LisaRating, 5 stars3 months ago
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!!
Top guest favourite
Home in Lake Geneva
5 out of 5 average rating, 33 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

DanielRating, 5 stars1 week ago
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.
Guest favourite
Home in Fontana-on-Geneva Lake
5 out of 5 average rating, 16 reviews

Abbey Springs Home! Hot Tub + Golf Cart

KathyRating, 5 stars1 month ago
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!
Guest favourite
Home in Madison
4.91 out of 5 average rating, 267 reviews

Luxurious BBQ and Pool House

ScottRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Lake Geneva
4.96 out of 5 average rating, 76 reviews

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD

BethRating, 5 stars1 day ago
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.
Superhost
Home in Lake Geneva
5 out of 5 average rating, 6 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

ADAMRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Whitewater
5 out of 5 average rating, 81 reviews

Nestled in the Southern Kettle Moraine Forest

DianaRating, 5 stars3 days ago
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.
Top guest favourite
Home in Genoa City
5 out of 5 average rating, 54 reviews

Relaxing Summer Getaway near Lake Geneva w/ Pool

BenjaminRating, 5 stars3 weeks ago
The house was a perfect fit for my family of 8. The amenities were great and Nicolet provided excellent communication.

Weekly house rentals

Top guest favourite
Home in Lake Mills
5 out of 5 average rating, 21 reviews

The Yellow Door Guest House-Lower

CassieRating, 5 stars1 week ago
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.
Top guest favourite
Home in Watertown
5 out of 5 average rating, 17 reviews

Blue House in the Pines

AmberRating, 5 stars1 month ago
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!
Superhost
Home in Stoughton
4.93 out of 5 average rating, 15 reviews

The Orchard House

JenniferRating, 5 stars1 month ago
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!
Guest favourite
Home in Glendale
4.92 out of 5 average rating, 25 reviews

Bass & Sparrow - Spa Retreat on the MKE River

CamilleRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Hartford
4.9 out of 5 average rating, 40 reviews

The Pike Lake Cottage House

LisaRating, 5 stars4 days ago
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.
Guest favourite
Home in Pewaukee
4.92 out of 5 average rating, 25 reviews

Bougie by the Beach

DeborahRating, 5 stars4 days ago
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.
Guest favourite
Home in Pewaukee
4.92 out of 5 average rating, 24 reviews

Pewaukee Lake Home steps from water & restaurants!

IlheeRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Palmyra
4.98 out of 5 average rating, 50 reviews

A-Frame in forest on bike trail!

JaneRating, 5 stars3 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!

Private house rentals

Superhost
Home in Waukesha
4.88 out of 5 average rating, 57 reviews

Cozy 3BR Ranch Home Away From Home

MardeeRating, 5 stars2 days ago
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!
Superhost
Home in Waukesha
5 out of 5 average rating, 4 reviews

Farmhouse "The Inn"

SaraRating, 5 stars10 months ago
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.
Top guest favourite
Home in Beaver Dam
5 out of 5 average rating, 13 reviews

The Gatsby Getaway- a Charming Lakeside Retreat

JamieRating, 5 stars1 week ago
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.
Top guest favourite
Home in Watertown
5 out of 5 average rating, 63 reviews

Watertown Family Retreat

TabithaRating, 5 stars4 days ago
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!
Top guest favourite
Home in Fort Atkinson
4.97 out of 5 average rating, 34 reviews

1891 Home - Steps to Downtown & Free Breakfast

AkiRating, 5 stars1 month ago
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.
Superhost
Home in Whitewater
4.7 out of 5 average rating, 10 reviews

Tranquil Wellness Retreat with Lake Views and Gym

GraciaRating, 5 stars1 month ago
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.
Top guest favourite
Home in Pewaukee
5 out of 5 average rating, 55 reviews

Luxury Lake Home-Miles of Lake Views-Private Pier

ShariRating, 5 stars1 month ago
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!
Top guest favourite
Home in Milton
5 out of 5 average rating, 69 reviews

Beautiful Lake Views While Lounging in the Hot Tub

KylieRating, 5 stars1 week ago
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

Destinations to explore

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