
Vacation rentals in Oconomowoc
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Top-rated vacation rentals in Oconomowoc
Guests agree: these stays are highly rated for location, cleanliness, and more.

Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

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

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

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.).

Beautiful home on Okauchee Lake, WI
I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

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.

YurtCation
YurtCation is a relaxing getaway with lake frontage and nature trails. There is another yurt about 300ft up the same driveway. There are a total of two yurts and two homes that have access to the same 17 acre lake. Each yurt is off the grid and has their own queen-sized comfy bed, wood stove, Weber grill w/charcoal, fire pit, firewood, fresh water, canoe, and clean Porto Potty. Pet Policy: Max two - Must be in your sight and supervised at all times or $500 fine and check out immediately.

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.

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.

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.

Charming Historic Upper•Walk to Downtown+Festivals
✨Experience a memorable Wisconsin getaway at the Blue Belle, a beautifully preserved Victorian home nestled in the heart of Lake Country. 📍This charming small town offers the perfect blend of adventure and relaxation, with shops, restaurants, wedding venues and activities all within walking distance. 🗓️Browse our host profile for additional listings if your preferred dates are unavailable or if you're traveling with a larger group or a 🐶furry friend.

Quiet Lake Country Retreat
Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.
Popular amenities for Oconomowoc vacation rentals
Other great vacation rentals in Oconomowoc

Oconomowoc Downtown River View

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Family friendly farmstay just outside Milwaukee

Pewaukee Serenity Cottage: Whimisical by the Lake

Cheerful, open space, and relaxing 1 bedroom home.

Modern Lake Country Farmhouse in Delafield

Cozy Lake Cottage With The Best View & Pontoon!

Clean 1bd/1bath close to everything!
When is the best time to visit Oconomowoc?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 148 | € 148 | € 167 | € 177 | € 216 | € 217 | € 247 | € 243 | € 215 | € 147 | € 149 | € 147 |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
Frequently Asked Questions
Where should I stay in Oconomowoc?
Make yourself at home in Oconomowoc by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Worthingtons, over 20 vacation rentals in Wren Crest, and over 20 vacation rentals in Summit.
Are there vacation rentals with a dedicated workspace in Oconomowoc?
Yes! Work meets play with ease at over 10 vacation rentals in Oconomowoc featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Oconomowoc?
Experience the best of Oconomowoc with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Oconomowoc?
Oconomowoc has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Oconomowoc have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oconomowoc have wifi?
Absolutely! We offer over 20 house rentals with wifi in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Oconomowoc

Total vacation rentals
Explore 20 vacation rentals in Oconomowoc

Nightly prices starting at
Oconomowoc vacation rentals start at € 52 per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Oconomowoc vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oconomowoc rentals

4.9 Average rating
Oconomowoc stays are highly rated by guests—averaging 4.9 out of 5!
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