A boat on a calm lake with a forested shoreline in the background.

Oconomowoc Vacation Rentals

Dates

November 2026

December 2026

Check prices for these dates

In two weeks

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Our top choices for Oconomowoc vacation rentals

A Staybridge Suites hotel with a brick facade, a central entrance with a covered porch, and a flagpole with an American flag.

1. Spacious Accessible Studio w/ Walk-In Shower

Oconomowoc

$160 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hot tub under a covered area with a wooden roof, surrounded by a white fence, trees, and a clear sky.

2. Private Hot Tub • Bright Home Near Downtown

Oconomowoc

Heather F.

$285 nightly

Nov 15 - Nov 16

Total with taxes and fees

3. Queen Studio Suite w/ Kitchenette in Oconomowoc

Oconomowoc

$160 nightly

Nov 15 - Nov 16

Total with taxes and fees

4. 2-BR Suite w/ King & Double Beds + Kitchen

Oconomowoc

Sharon J.

$283 nightly

Nov 15 - Nov 16

Total with taxes and fees

5. Accessible 1-BR Queen Suite w/ Roll-In Shower

Oconomowoc

$185 nightly

Nov 15 - Nov 16

Total with taxes and fees

6. Accessible 1-BR Suite w/ Two Double Beds

Oconomowoc

$185 nightly

Nov 15 - Nov 16

Total with taxes and fees

7. Accessible 1BR Suite | Pool & Daily Breakfast

Oconomowoc

$185 nightly

Nov 15 - Nov 16

Total with taxes and fees

8. Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

Oconomowoc

Rhonda M.

$283 nightly

Nov 22 - Nov 23

Total with taxes and fees

9. Accessible 2-BR Suite w/ Tub & 2 Bathrooms

Oconomowoc

$283 nightly

Nov 15 - Nov 16

Total with taxes and fees

A brick building with a sign for Riverview Lodges and a Green Door Café.

10. Historic Downtown Luxury-Lake-Coffee-Spa like BA

Delafield

Becky M.

$215 nightly

Nov 10 - Nov 11

Total with taxes and fees

A cozy room with a wooden ceiling, a black sofa with colorful cushions, a round coffee table with flowers, and a black chair.

11. Historic Downtown- King Bed-St Johns Acad-Shopping

Delafield

Holly L.

$267 nightly

Nov 10 - Nov 11

Total with taxes and fees

12. Relax & Reboot in this Charming 2-Bedroom Townhome

Ixonia

Jon S.

$359 nightly

Nov 10 - Nov 11

Total with taxes and fees

13. Historic Downtown-Old World Charm-Dining-Coffee

Delafield

Jeffrey C.

$247 nightly

Nov 12 - Nov 13

Total with taxes and fees

A two-story house with a front porch, a chimney, and a garage.

14. 4 bedroom house 7 min.to Erin Hills SAND VALLEY GOLF COURSE HOLY HILL WHISTLING

Hartford

$1,119 nightly

Nov 15 - Nov 16

Total with taxes and fees

A log cabin with a stone foundation, a large garage, and a well-maintained lawn.

15. Rustic Charm: Pewaukee Lake Cabin, Sauna & Hot Tub

Pewaukee

Danny H.

$1,215 nightly

Nov 15 - Nov 16

Total with taxes and fees

A room with a wooden floor, a red sofa, a small table with a lamp, and a painting on the wall.

16. King Bed! Family-Friendly, Minutes from Holy Hill, Hiking+Skiing + Golf

Hartford

Shawn T.

$327 nightly

Nov 13 - Nov 14

Total with taxes and fees

A modern kitchen with a stainless steel refrigerator, a black stove, and wooden flooring.

17. 3BR Home Near Hahns Lake – Newly Updated Kitchen

Johnson Creek

D M.

$310 nightly

Nov 16 - Nov 17

Total with taxes and fees

A hotel room with a bed, a bathroom with a large mirror, a sink, and a window.

18. 1 Queen Bed | Non-Smoking, Kitchen

Milwaukee WI

Laurie

$75 nightly

Nov 18 - Nov 19

Total with taxes and fees

A spacious interior with a stone staircase, a large window, and a cozy seating area.

19. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Hubertus

Humphries D.

$678 nightly

Nov 10 - Nov 11

Total with taxes and fees

A wooden deck with a glass railing overlooking a snowy landscape with trees.

20. Eclectic Hubertus Home w/ Game Room & Fire Pit!

Hubertus

$732 nightly

Nov 10 - Nov 11

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Oconomowoc Hotel Reviews

A Staybridge Suites hotel with a prominent entrance, flagpoles, and a well-lit facade.

Staybridge Suites Milwaukee West-Oconomowoc by IHG

Oconomowoc

10/10 Excellent

Lori Lyn

An outdoor patio with wicker furniture, a fire pit, and a grill area.

TownePlace Suites by Marriott Oconomowoc

Oconomowoc

10/10 Excellent

Kent

A Victorian-style house with a prominent front entrance, a steeply pitched roof, and a brick facade.

Mon Bijou

Oconomowoc

10/10 Excellent

Zach

A spacious indoor area with large windows, a central table, and multiple seating arrangements.

Hilton Garden Inn Oconomowoc

Oconomowoc

10/10 Excellent

Kerry

A spacious living area with a fireplace, seating, and large windows.

Holiday Inn Express & Suites Delafield by IHG

Delafield

10/10 Excellent

Shelley

A cozy interior with a wooden staircase, a coffee station, and a dining area.

The Katherine Holle House

Watertown

10/10 Excellent

Anonymous traveler

A dining table set for breakfast with chairs, plates, cups, and a glass of orange juice.

Shane Acres Country Inn

Juneau

10/10 Excellent

Can't wait until I can go back in warm weather to use their beautiful outdoor pool, & the hot tub (the hot tub is available year-round but some work had to be done on it). I was very hedonistic & enjoyed the solitude of the jacuzzi in my own room, and it was lovely to be able to watch the marsh go to sleep, then reawaken in the morning, all from the comfy coziness of my own room . The full body hammock-type tree swings were such a treat, too; overall, this was a much-needed healing retreat for...

Lisa

A modern hotel building with a prominent 'Avid' sign, large windows, and a covered entrance area.

avid hotel Milwaukee West Waukesha by IHG

Pewaukee

10/10 Excellent

I needed to cancel the day of because of Covid. Hotels.com would not refund unless the hotel management agreed. I believe Latoya was the very kind woman who helped me convince management to issue me a refund. Big thanks to management and Latoya as this booking was for my mother who cannot afford to waste money on unused hotel nights. I will go out my way to sleep here anytime I visit Milwaukee. Hopefully the accommodations match the front desk service.

Irene

A modern hotel lobby with seating areas, a TV screen, and a coffee station.

Best Western Watertown

Watertown

10/10 Excellent

Kelly

A hotel with a row of single-story buildings, a parking lot, and a well-lit sign.

La Quinta Inn & Suites by Wyndham Milwaukee Delafield

Delafield

10/10 Excellent

Christine

A modern living room with a fireplace, comfortable seating, and a large window offering a city view.

Residence Inn by Marriott Milwaukee Brookfield at Poplar Creek

Brookfield

10/10 Excellent

Ava

A modern lobby with a stone wall, a fireplace, and two yellow armchairs.

Marriott Milwaukee West

Waukesha

10/10 Excellent

Jennifer

An outdoor seating area with wicker furniture and blue cushions, adjacent to a building with large windows and a brick facade.

Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

Brookfield

10/10 Excellent

Christopher

A residential building with a sign reading "Residence Inn by Marriott."

Residence Inn By Marriott Milwaukee Brookfield

Brookfield

10/10 Excellent

Anonymous traveler

A modern hotel with a prominent entrance, multiple floors, and a well-lit facade.

Hilton Garden Inn Milwaukee Brookfield Conference Center, WI

Brookfield

10/10 Excellent

Amber

Fairfield Inn & Suites by Marriott Whitewater

Whitewater

10/10 Excellent

Mark

A room with two metal-framed lounge chairs, one with a towel on it, and a small table with a towel and a rolled-up item.

Holiday Inn Pewaukee - Milwaukee West by IHG

Pewaukee

10/10 Excellent

Anonymous traveler

Find out more about Oconomowoc

Everything you need to know about Oconomowoc vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oconomowoc vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oconomowoc vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oconomowoc vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oconomowoc. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Oconomowoc in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $84 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oconomowoc rentals

At Expedia, we put the best Oconomowoc vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Oconomowoc rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oconomowoc vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oconomowoc. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Oconomowoc?

Yes, we offer vacation rentals in Oconomowoc close to Fowler Lake Park, or you can choose a more secluded option if you want a relaxing stay. The shops and restaurants are several reasons why visitors like Oconomowoc. Make sure you have time to check out the cafes and sporting events during your trip.

What are some of the best vacation rentals that Oconomowoc has to offer?

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle: This highly rated vacation home rental in Oconomowoc is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. Other favorite homes for rent in Oconomowoc are Beautiful Historic Tudor Mansion with sandy Private Beach and Sunset Lake House w Hot Tub, 4 fireplaces & kids bunkroom!.

How many vacation rentals are there in Oconomowoc?

With 25 Expedia vacation rentals, you're sure to find just the right place for your Oconomowoc stay.

What’s there to see and do in Oconomowoc?

Enjoy the outdoors at Fowler Lake Park and Lac La Belle, or simply take in cultural attractions like Oconomowoc Arts Center and Theatre On Main. Other places in town to visit include Oconomowoc Golf Club and Lake Okauchee.

What’s a vacation rental in Oconomowoc like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Oconomowoc. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for small groups.

Explore a world of travel with Expedia

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