House vacation rentals in Oconomowoc

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Popular amenities for Oconomowoc house rentals

House rentals with a pool

Guest favorite
Home in Brewer's Hill
4.92 out of 5 average rating, 140 reviews

The Gem of Brewers Hill w/hot tub & seasonal pool

GerryRating, 5 stars3 weeks ago
Excellent location and plenty of beds and bathrooms.
Top guest favorite
A single-story house is presented with a light exterior and a welcoming porch. A shaded area is provided by the overhanging roof, and a bench is positioned on the porch. A well-maintained lawn stretches in front, framed by lush green trees.
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!!
Guest favorite
An outdoor seating area features a wooden picnic table with benches, surrounded by colorful autumn trees. A grill is covered nearby, and a glimpse of the pool can be seen in the background. The deck provides a spacious area for relaxation and gatherings.
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 favorite
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!
Top guest favorite
Two black Adirondack chairs and a small side table are positioned on a patio, overlooking a lush green landscape under a cloudy sky. The view encompasses rolling hills and tree foliage, providing a serene outdoor setting.
Home in Lake Geneva
5 out of 5 average rating, 40 reviews

Newly Updated Modern Lake Condo

LaurenRating, 5 stars4 weeks ago
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!
Guest favorite
A spacious outdoor pool area is presented, surrounded by a clean concrete deck. Several round tables with chairs are arranged around the pool, providing seating. Lush greenery and trees are visible in the background, contributing to a serene environment.
Home in Lake Geneva
4.96 out of 5 average rating, 74 reviews

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

SarahRating, 5 stars2 days ago
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!
Superhost
The backyard features a large in-ground pool surrounded by a wooden deck, adorned with comfortable seating areas and a pergola. Lush greenery frames the space, contributing to a peaceful atmosphere. Sunlight reflects off the water, offering a refreshing contrast to the well-maintained surroundings.
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 favorite
Home in Whitewater
5 out of 5 average rating, 80 reviews

Nestled in the Southern Kettle Moraine Forest

VictoriaRating, 5 stars4 weeks ago
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

Top guest favorite
The two-story house features a grey exterior with a gabled roof and decorative shingles. A welcoming front porch is adorned with seasonal decorations, including small pumpkins. A well-maintained lawn and a stone pathway lead to the entrance, surrounded by lush greenery and trees.
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 favorite
A blue cottage is framed by lush greenery and trees, featuring a stone patio with outdoor seating and an umbrella. Sunlight casts gentle shadows, highlighting the inviting entrance and landscaped surroundings.
Home in Watertown
5 out of 5 average rating, 17 reviews

Blue House in the Pines

AmberRating, 5 stars4 weeks 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
The Orchard House is illuminated against a twilight sky, showcasing its wooden exterior. Large glass doors reveal a cozy interior with soft glowing lights. A tranquil setting is framed by surrounding trees and open grassland.
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 favorite
The exterior of a renovated farmhouse features a covered porch with large windows, allowing for natural light. A well-maintained lawn and garden area are present, with a stone pathway leading to the entrance. The house showcases a combination of white siding and dark trim.
Home in Pewaukee
4.92 out of 5 average rating, 25 reviews

Bougie by the Beach

DeborahRating, 5 stars1 day 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 favorite
The front view of the cottage displays a charming exterior, featuring a combination of light-colored wooden siding and stone accents. A wooden porch with a railing leads to the entrance, and a circular wreath adorns the front door. Large windows allow natural light into the living space.
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 favorite
A spacious living room features natural light flowing through large windows. A comfortable gray sofa is positioned alongside two armchairs, creating a cozy seating area. A light-colored area rug covers the hardwood floor, and a lamp provides additional illumination in the corner.
Home in Watertown
5 out of 5 average rating, 63 reviews

Watertown Family Retreat

TabithaRating, 5 stars2 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 favorite
An intimate loft space features a cozy sectional sofa with a light grey hue, accompanied by a round coffee table in the center. Sky lights allow natural light to illuminate the deep blue walls, while a framed horse print adds a touch of character. A separate sleeping area can be glimpsed through a doorway.
Home in Wauwatosa
5 out of 5 average rating, 18 reviews

Auburn Place: Cozy 3BR Home in Wauwatosa

J BlairRating, 5 stars5 days ago
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.
Top guest favorite
The exterior of the classic A-frame cabin, featuring a striking red facade, is set against a backdrop of lush greenery. A wooden walkway leads to a seating area with two chairs. A deck is visible, providing an inviting space to relax outdoors.
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

Guest favorite
A well-lit bedroom features a spacious bed dressed in crisp white linens, layered with a navy blue blanket and yellow accent pillows. Natural light enters through two windows, adorned with bright yellow curtains. A wooden dresser and a mirror provide functional space, complemented by a decorative wall art piece.
Home in Hartford
4.94 out of 5 average rating, 36 reviews

Convenient, NFL Draft,Holy Hill, Golf, Skiing

AndrewRating, 5 stars2 weeks ago
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
Top guest favorite
A spacious living area features a cozy seating arrangement with two yellow chairs and a small side table. An open kitchen can be seen in the background, accompanied by a breakfast bar with blue stools. Natural light floods in through large windows, highlighting the warm wood tones.
Home in Bluemound Heights
5 out of 5 average rating, 73 reviews

Entire Cozy Cottage! Pet Friendly, No Cleaning Fee

KateRating, 5 stars1 week ago
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!
Superhost
The exterior of the stone farmhouse features a charming fenced area with a patio, shaded by an umbrella. Large windows adorn the building, allowing natural light to illuminate the inviting stone facade. Lush greenery surrounds the entrance, enhancing the serene atmosphere.
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.
Guest favorite
The living area features vaulted ceilings, providing an open feel. A sectional couch and armchair are arranged around a central ottoman, with a dining table nearby. Large windows allow natural light to fill the space, offering views of the outdoors.
Home in Mukwonago
4.94 out of 5 average rating, 53 reviews

Relaxing Lake House Getaway on Phantom Lake

SusieRating, 5 stars3 weeks ago
We had a great stay while visiting Wisconsin
Guest favorite
The cottage exterior is showcased with a welcoming design, featuring a stone foundation and a charming yellow upper section. A large sunroom with multiple windows provides ample natural light and views of the surroundings. Lush green grass surrounds the structure, enhancing the outdoor appeal.
Home in Hartford
4.9 out of 5 average rating, 40 reviews

The Pike Lake Cottage House

LisaRating, 5 stars1 day 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.
Top guest favorite
The exterior of a renovated 1895 home is shown, featuring a white façade with red shutters. A well-maintained lawn surrounds the property, with a small flowerbed at the base. A flag hangs from the porch, while a staircase leads to the main entrance.
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
A serene view of a well-maintained lawn leads to a sparkling body of water, surrounded by trees. A patio table and chairs sit on the stone surface, with a subtle path of stepping stones leading towards the greenery. Bright natural light casts gentle shadows across the scene.
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 favorite
A serene view of Pewaukee Lake is captured, featuring a large tree on the lawn and multiple docks lined along the water's edge. The sky is adorned with soft clouds reflecting colorful hues, complementing the peaceful lake setting.
Home in Pewaukee
5 out of 5 average rating, 55 reviews

Luxury Lake Home-Miles of Lake Views-Private Pier

ShariRating, 5 stars4 weeks 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!

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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