Luxury Vacation Rentals in Oconomowoc

Luxury Vacation Rentals in Oconomowoc

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 2 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

Welcome to Oconomowoc

Welcome to Oconomowoc

Welcome to Wander in Wisconsin’s Lake Country, where our luxury vacation rentals in Oconomowoc pair hotel polish with the privacy of a beautiful home. Expect spaces that look exactly like the photos, operated by professionals who sweat every detail.
Each residence delivers ultra fast WiFi, pristine cleaning, premium linens, and 24/7 concierge support. Enjoy generous living areas, sleek kitchens for effortless cooking, and thoughtfully designed nooks for focus or downtime. Many homes offer fitness gear and inviting outdoor zones for fresh-air breaks.
Book with confidence and settle into a refined retreat crafted for work, celebration, and everything between.

Available soon in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

All homes in Oconomowoc

Sytlish Retreat Near Wedding Venues + Downtown property photo 1

Sytlish Retreat Near Wedding Venues + Downtown

3 bedrooms•2 baths
1,124 US dollars for 3 nights•

~$100 less than other sites

Charming Historic Upper Walk to Downtown & Lakes property photo 1

Charming Historic Upper Walk to Downtown & Lakes

3 bedrooms•2 baths
879 US dollars for 3 nights•

~$75 less than other sites

View all homes

Highlights in Oconomowoc

Experience the charm of Oconomowoc, a historic lakefront destination offering vibrant downtown streets, scenic boardwalks, and year-round outdoor adventures.
City Beach on Lake La Belle
Fowler Lake Park and Boardwalk
Kettle Moraine State Forest - Lapham Peak
Downtown Oconomowoc Historic District
Oconomowoc Arts Center
The Club at Lac La Belle

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Oconomowoc

Lake access (1)
Beach access (1)
Sound system (1)
Hammock (1)
Fire pit (1)
Dryer (2)
Patio (1)
Oven (2)
Washer (2)
Garden (1)
Kitchen (2)
Tv (2)
Outdoor dining area (1)
Wifi (2)
Microwave (2)
Heating (2)

Other popular amenities & vacation types in Oconomowoc

Family vacation rentals in Oconomowoc
Discover more of Oconomowoc

Discover more of Oconomowoc

Set in Wisconsin’s Lake Country, Oconomowoc is ringed by clear lakes that set the pace for every season. Summer brings boat rides, paddleboards, and sunlit piers. Autumn paints the shoreline in deep reds and golds, while winter swaps sails for skates and cozy evenings fireside.
Explore a walkable downtown rich with historic architecture, indie boutiques, and a lively arts calendar. Ride the Lake Country Trail, tee off nearby, or slip into Kettle Moraine for glacial views. Milwaukee sits within easy reach, yet Oconomowoc keeps its unhurried charm. This is why Wander's luxury vacation rentals in Oconomowoc are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Oconomowoc

Why should I book a Wander in Oconomowoc over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Oconomowoc delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Oconomowoc?

Some of our most popular vacation rentals in Oconomowoc include Sytlish Retreat Near Wedding Venues + Downtown, Charming Historic Upper Walk to Downtown & Lakes, and Sytlish Retreat Near Wedding Venues + Downtown. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Oconomowoc?

Wander offers 2 vacation rentals in Oconomowoc, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Oconomowoc?

You can check-in to Wander vacation rentals in Oconomowoc after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Oconomowoc have WiFi access?

Yes. Every Wander home in Oconomowoc has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.