
Holiday rentals in Oconomowoc
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Top-rated holiday 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.

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.

Oconomowoc Downtown River View
Stunning view of the Oconomowoc river, locate in the heart of downtown Oconomowoc. Whether you are traveling for fun or work there is something for everyone. Walk to sandy beaches, six nearby parks, tennis court, or just walk around beautiful Lac La Belle Lake and Fowler Lake. Bring your kayaks or boat. Local boat rentals are available in town. Enjoy live bands and events at restaurants and bars or have a peaceful dinner at one of many fine dining restaurants also in walking distance.

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.

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.

Cozy Cottage Lake Country
Welcome to our newly renovated two-bedroom cottage nestled in the heart of Lake Country! This cozy retreat boasts a living area with a fireplace, a fully equipped kitchen, a dining nook, a dedicated workspace, and modern amenities. Located conveniently between Milwaukee and Madison, you’ll find yourself surrounded by multiple lakes, hiking and biking trails, shopping, dining, festivals, and a plethora of other activities.

Okauchee Lakefront Cabin Escape
The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.
Popular amenities for Oconomowoc holiday rentals
Other great holiday rentals in Oconomowoc

The Orchard Room-Quiet Private Suite Near Milw

2BR Sapphire Summit Suite w/ Bar – Brookfield

Whitewater Night Lodging

Okauchee Lake - Relax/Entertain

Stay in one of the most beautiful towns in WI.

Historic Hawthorne House

Serene Cottage in Center of Milw/Tosa (for women)

Maura room 1
When is the best time to visit Oconomowoc?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $223 SGD | $223 SGD | $253 SGD | $267 SGD | $326 SGD | $329 SGD | $373 SGD | $368 SGD | $325 SGD | $222 SGD | $226 SGD | $222 SGD |
| 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 Wren Crest, over 20 vacation rentals in Summit, and over 20 vacation rentals in Worthingtons.
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 $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Are there family-friendly house rentals in Oconomowoc?
Oconomowoc has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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 holiday rentals in Oconomowoc

Total holiday rentals
Explore 20 holiday rentals in Oconomowoc

Nightly prices starting at
Oconomowoc holiday rentals start at $78 SGD per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Oconomowoc holiday rentals include wifi 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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