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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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Cottage in Hartland

4.95 out of 5 average rating, 132 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.).

Rental unit in Watertown

4.97 out of 5 average rating, 228 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.

Home in Watertown

4.93 out of 5 average rating, 146 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.

Yurt in Cambridge

4.97 out of 5 average rating, 574 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.

Townhouse in Waukesha

4.92 out of 5 average rating, 122 reviews

Remodeled 2 bedroom 1 bath private home

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.

Home in Wales

4.95 out of 5 average rating, 118 reviews

Charming, Updated and Historic

This is truly a memorable, charming, and welcoming place to stay. You will have the home to yourself. You will love the warm feel, woodwork, and historical prominence of this home. It is very charming throughout and is on a large 1.5-acre estate size lot. The price quoted here is for 1-2 people and a 1 Bedroom suite with 1.5 Baths. Under this listing we can open up to three suites and accept six guests. If need more there than 2 guests and 1 suite we are happy to make you a custom offer.

Cabin in Fox Lake

4.96 out of 5 average rating, 164 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 pet fee/stay.

Home in Delafield

4.96 out of 5 average rating, 164 reviews

Nagawicka Woods-Beautiful Lake Country Ranch Home

Welcome to Nagawicka Woods, a beautiful home located in Delafield, WI in the heart of Lake Country. Minutes from lake access to: Nagawicka, Okauchee, Pewaukee, Pine, Namahbin & Oconomowoc Lakes. 2 blocks from St. John's NW Military Academy, 6 minutes from Rogers Memorial Hospital, half an hour from Milwaukee & one hour from Madison. This home sleeps 6 (a pack n play is available.) Ideal for couples, family, small groups or a girlfriends getaway. Set on a quiet 1.5 private acres.

Guest suite in Sussex

4.96 out of 5 average rating, 276 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.

Guest suite in Sussex

4.99 out of 5 average rating, 136 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.

Guest suite in Deerfield

4.94 out of 5 average rating, 107 reviews

Studio on the Prairie Fen

Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

Rental unit in Elkhorn

4.94 out of 5 average rating, 373 reviews

FarmWise Country Stay by Alpine Valley/Lake Geneva

Retreat to a quiet countryside experience at this all organic farm, where you can sit back, relax, and enjoy the country charm of your private space inside the main farm house. Optional for you are joining us for early morning chores in the barn. If you tell me the night before, you can try milking Carmel, the cow by hand, feeding the pig, collecting eggs from the chicken coop and more. Most loved of all are our friendly cats!

Vacation rentals for every style

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Popular amenities for Oconomowoc vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Oconomowoc's top sights

Weissgerber's Golden Mast Inn8 locals recommend

Bella Gusto Restaurant And Italian Market & Pizzeria7 locals recommend

Foolery's5 locals recommend

Piggly Wiggly5 locals recommend

City Beach5 locals recommend

Roots Coffeebar & Cafe5 locals recommend

Other great vacation rentals in Oconomowoc

Home in Nashotah

4.97 out of 5 average rating, 67 reviews

Okauchee Lakefront Cabin Escape

Home in Hartford

4.94 out of 5 average rating, 31 reviews

Convenient, NFL Draft,Holy Hill, Golf, Business

Home in Nashotah

4.94 out of 5 average rating, 66 reviews

Beautiful home on Okauchee Lake, WI

Cottage in Hustisford

5 out of 5 average rating, 57 reviews

Charming Lakeside Cottage

Home in Watertown

5 out of 5 average rating, 39 reviews

Watertown Family Retreat

Home in Oconomowoc

4.85 out of 5 average rating, 13 reviews

Lake Country Haven

Home in Waukesha

4.99 out of 5 average rating, 79 reviews

Brand New Studio w. Private Entry + Garden Patio

Home in Watertown

4.89 out of 5 average rating, 19 reviews

Modern Comfort in the Heart of Watertown

Quick stats about vacation rentals in Oconomowoc

Total rentals
20 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
840 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

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 Summit, over 20 vacation rentals in Wren Crest, 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 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 20 house rentals with wifi in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore