Oconomowoc vacation rentals

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Top-rated vacation rentals in Oconomowoc

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Wales

4.92 out of 5 average rating, 146 reviews

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

Jan 2 – 9

G$31,925 GYD per night

Guest favorite

Guest suite in Brookfield

4.99 out of 5 average rating, 182 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Relax "in the Canopy" of beautiful maples! We’re a Superhosted, verified Guest Favorite, available for the GOP Convention! A comfortable retreat in a tree-filled neighborhood, just a few minutes from all the best Milwaukee has to offer. Perfect location for quick access to the city, or to Lake Country to the west. Quiet, comfortable, safe, surrounded by beautiful gardens. We’re in a perfect launching spot to visit Summerfest, Brewers/Bucks games, or Milwaukee's western suburbs. Bring the kids!

May 30 – Jun 6

G$23,826 GYD per night

Guest favorite

Home in Oconomowoc

4.92 out of 5 average rating, 142 reviews

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Sep 21 – 28

G$41,902 GYD per night

Guest favorite

Cottage in Hartland

4.96 out of 5 average rating, 112 reviews

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.).

Jul 9 – 16

G$42,290 GYD per night

Guest favorite

Apartment in Watertown

4.97 out of 5 average rating, 203 reviews

The Ernest Inn - Located downtown Watertown

Welcome to the perfect "home" away from home. This apartment is located in a historical building in the heart of downtown Watertown right on Main Street. This apartment features a complete kitchen, a working typewriter, a record player, a collection of classic vinyl, wifi, a smart tv, a brand new stone tile bathroom, and a back porch to relax and take in the sounds of downtown. This apartment is perfect for just one or two but can accommodate up to 6 guests. Licensed, insured, and inspected.

Oct 4 – 11

G$27,243 GYD per night

Guest favorite

Home in Watertown

4.97 out of 5 average rating, 124 reviews

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.

Feb 8 – 15

G$27,454 GYD per night

Guest favorite

Yurt in Cambridge

4.97 out of 5 average rating, 544 reviews

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.

Mar 2 – 9

G$28,350 GYD per night

Guest favorite

Cabin in Fox Lake

4.95 out of 5 average rating, 122 reviews

Cabin on the Trail

Kick back and relax in this cozy space with up north, cabin vibes. In the summer months enjoy the excellent fishing, swimming and boating and in the winter have fun ice fishing by walking to the lake out your back door! *Please read the full description and look at all of the pictures of the property *Not suitable for parties or loud gatherings. Please note, there is a 4 person maximum, including children. *All dogs/pets must be pre-approved by the host. There is a $50 fee/stay.

Mar 2 – 9

G$22,394 GYD per night

Guest favorite

Guest suite in Sussex

4.96 out of 5 average rating, 237 reviews

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.

Mar 24 – 31

G$21,121 GYD per night

Guest favorite

Guest suite in Sussex

4.99 out of 5 average rating, 124 reviews

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.

Sep 18 – 25

G$30,400 GYD per night

Guest favorite

Farm stay in US

4.98 out of 5 average rating, 181 reviews

Family friendly farmstay just outside Milwaukee

The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

Jan 6 – 13

G$22,984 GYD per night

Guest favorite

Cabin in Whitewater

4.94 out of 5 average rating, 288 reviews

Glamping Cabin on Cold SpringTree Farm

Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.

Sep 19 – 26

G$19,112 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oconomowoc vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Oconomowoc's top sights

Crafty Cow3 locals recommend

Kiltie Drive-In3 locals recommend

Piggly Wiggly5 locals recommend

Bella Gusto Restaurant And Italian Market & Pizzeria7 locals recommend

Roots Coffeebar & Cafe5 locals recommend

Pick 'n Save5 locals recommend

Other great vacation rentals in Oconomowoc

Guest favorite

Home in Campbellsport

4.99 out of 5 average rating, 136 reviews

Gleason's Chouse

Aug 11 – 18

G$26,699 GYD per night

Guest favorite

Home in Delafield

4.97 out of 5 average rating, 156 reviews

Nagawicka Woods-Beautiful Lake Country Ranch Home

Dec 11 – 18

G$39,303 GYD per night

Guest favorite

Guesthouse in East Troy

4.86 out of 5 average rating, 304 reviews

Deligo Valley Cottage

Jan 4 – 11

G$28,381 GYD per night

Guest favorite

Home in Delafield

4.99 out of 5 average rating, 108 reviews

Modern Lake Country Farmhouse in Delafield

Nov 23 – 30

G$45,159 GYD per night

Superhost

Cabin in Edgerton

4.89 out of 5 average rating, 197 reviews

The Overlook on Lake Koshkonong - Custom Log Cabin

Jan 6 – 13

G$23,286 GYD per night

Guest favorite

Condo in Lake Geneva

4.93 out of 5 average rating, 424 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Apr 26 – May 3

G$22,415 GYD per night

Guest favorite

Home in Oconomowoc

4.89 out of 5 average rating, 19 reviews

Oconomowoc Downtown River View

Jan 20 – 27

G$26,612 GYD per night

Guest favorite

Apartment in Oconomowoc

4.92 out of 5 average rating, 24 reviews

The Daytime-Come Stay The Night

Oct 6 – 13

G$43,196 GYD per night

Show all

Other great vacation rentals in Oconomowoc

Guest favorite

Home in Oconomowoc

5.0 out of 5 average rating, 28 reviews

Cozy renovated historic home boasts 4 fireplaces

Nov 4 – 11

G$123,754 GYD per night

Guest favorite

Home in Oconomowoc

5.0 out of 5 average rating, 24 reviews

Luxury Lake Home & Pier-124' of Swimming Frontage

Dec 13 – 20

G$95,851 GYD per night

Guest favorite

Home in Oconomowoc

4.94 out of 5 average rating, 17 reviews

The Paddle House

May 11 – 18

G$69,102 GYD per night

Guest favorite

Apartment in Delafield

5.0 out of 5 average rating, 11 reviews

Historic Downtown Luxury-Lake-Coffee-Spa like BA

Jun 1 – 8

G$38,031 GYD per night

Guest favorite

Guest suite in East Troy

5.0 out of 5 average rating, 36 reviews

Mini Moon Hideaway

Apr 19 – 26

G$19,792 GYD per night

Guest favorite

Home in Waukesha

4.92 out of 5 average rating, 86 reviews

Remodeled 2 bedroom 1 bath private home

Sep 10 – 17

G$31,850 GYD per night

Guest favorite

Home in Nashotah

5.0 out of 5 average rating, 43 reviews

Okauchee Lakefront Cabin Escape

Oct 8 – 15

G$120,524 GYD per night

Guest favorite

Home in Menomonee Falls

4.93 out of 5 average rating, 70 reviews

Exhale, rest

Mar 16 – 23

G$28,187 GYD per night

Show all

Quick stats about vacation rentals in Oconomowoc

Total rentals
20 properties
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability
20 properties include access to wifi
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
690 reviews
Nightly prices starting at
G$10,445 GYD before taxes and fees

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 10 vacation rentals in Worthingtons, over 10 vacation rentals in Summit, and over 10 vacation rentals in Wren Crest.
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 10 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 10 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 10 house rentals with wifi in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oconomowoc?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Oconomowoc vacation rentals

Top-rated vacation rentals in Oconomowoc

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Oconomowoc vacation rentals

Stay near Oconomowoc's top sights

Other great vacation rentals in Oconomowoc

Home in Campbellsport

Home in Delafield

Guesthouse in East Troy

Home in Delafield

Cabin in Edgerton

Condo in Lake Geneva

Home in Oconomowoc

Apartment in Oconomowoc

Other great vacation rentals in Oconomowoc

Home in Oconomowoc

Home in Oconomowoc

Home in Oconomowoc

Apartment in Delafield

Guest suite in East Troy

Home in Waukesha

Home in Nashotah

Home in Menomonee Falls

Quick stats about vacation rentals in Oconomowoc

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Oconomowoc?

How much does it cost to stay in house rentals in Oconomowoc?

Do house rentals in Oconomowoc have air conditioning?

Are there family-friendly house rentals in Oconomowoc?

Do house rentals in Oconomowoc have wifi?

What are the most popular amenities for House Rentals in Oconomowoc?

Destinations to explore