Oconomowoc Vacations from $731
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The Latest Oconomowoc Vacation Packages
- Kinn Guesthouse Downtown
Oct 16 - Oct 19Kinn Guesthouse Downtown + Flight
Downtown Milwaukee2 nights4.5 star property9.4/10 - Exceptional (391 reviews)"Great place, first impression I wasn’t sure if I was in the right place since it was booked for me. Beautiful building, built in the 1800s. Rooms are amazing. Since it is in downtown Milwaukee, it does get a little loud but it’s to be expected. We’ll definitely stay here again."Reviewed July 30, 2026Roundtrip • Los Angeles (LAX) - Milwaukee (MKE)LAX - MKE • 1 stop MKE - LAX • 1 stop$877$731found 1 day agoper traveler - The Pfister Hotel
Sep 25 - Sep 28The Pfister Hotel + Flight
Downtown Milwaukee3 nights4.5 star property9.6/10 - Exceptional (2,207 reviews)"Old World Gem Great Place to stay !"Reviewed August 7, 2026Roundtrip • Atlanta (ATL) - Milwaukee (MKE)ATL - MKE • Nonstop MKE - ATL • Nonstop - Saint Kate - The Arts Hotel
Sep 25 - Sep 28Saint Kate - The Arts Hotel + Flight
Downtown Milwaukee3 nights4.0 star property9.8/10 - Exceptional (2,661 reviews)Roundtrip • Atlanta (ATL) - Milwaukee (MKE)ATL - MKE • Nonstop MKE - ATL • Nonstop - Kinn Guesthouse Bay View
Sep 23 - Sep 26Kinn Guesthouse Bay View + Flight
Bay View3 nights4.5 star property9.4/10 - Exceptional (496 reviews)"This was our second stay here, and unfortunately many of the same issues remained. The check-in process was still frustrating—I never received the access code and had to call to get it. I was told that because I booked through a third-party site, they didn't receive my information to send the code. Regardless of how the reservation is made, guests should receive the information they need before arrival. The concept of this place is great, but the execution is very poor. The room showed a lack of..."Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - Milwaukee (MKE)ATL - MKE • Nonstop MKE - ATL • Nonstop$1,127$951found 1 day agoper traveler - Landing Apartments at Mayfair Collection
Oct 28 - Nov 1Landing Apartments at Mayfair Collection + Flight
Wauwatosa4 nights4.0 star property10/10 - Exceptional (4 reviews)"Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance. We highly recommend staying here and will definitely be returning for a longer extended stay!"Reviewed May 21, 2026Roundtrip • Atlanta (ATL) - Milwaukee (MKE)ATL - MKE • Nonstop MKE - ATL • Nonstop$944$805found 1 day agoper traveler
Where to stay in Oconomowoc
Maplewood
Though Maplewood might not have many top sights, you can venture to the surrounding area to see attractions like Oconomowoc Golf Club and Lake Okauchee.
Lac La Belle Manor
Lac La Belle Manor might not have many top sights, but Lac La Belle and Fowler Lake Park are two attractions nearby that you can check out.
Peninsular Park
Peninsular Park might not have many top sights, but Hawks Inn and Nagawaukee County Park and Beach are two attractions nearby that you can check out.
Discover the most popular places to visit in Oconomowoc
Oconomowoc Hotel Deals
Staybridge Suites Milwaukee West-Oconomowoc by IHG
Staybridge Suites Milwaukee West-Oconomowoc by IHG
TownePlace Suites by Marriott Oconomowoc
TownePlace Suites by Marriott Oconomowoc"Very clean and spacious, will stay there again!"
"Staff was outstanding and the room was great. Would highly recommend staying there and will again. "
AmericInn by Wyndham Delafield-Waukesha-Milwaukee
AmericInn by Wyndham Delafield-Waukesha-Milwaukee"Unfortunately not the best stay. Cockroaches were in our room with purple stains all over the carpet. This hotel was close to a wedding venue which is why we picked it. The staff were friendly"
La Quinta Inn & Suites by Wyndham Milwaukee Delafield
La Quinta Inn & Suites by Wyndham Milwaukee Delafield"A/C unit was very loud !"
Holiday Inn Express & Suites Delafield by IHG
Holiday Inn Express & Suites Delafield by IHG
Days Inn by Wyndham Johnson Creek
Days Inn by Wyndham Johnson Creek"Great if you drive an EV: although the hotel offers no charging opportunities (boo), it’s right next door to a KwikTrip with a full array of high speed Tesla chargers. Location, location!! HVAC substandard: individual room cooling keeps the rooms perpetually damp."
Frequently Asked Questions
How much does an Oconomowoc vacation package cost?
You'll find cheap prices from $731 on Expedia for your Oconomowoc escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Oconomowoc costs.
What are the cheapest months to go to Oconomowoc?
You can generally find reduced prices and better availability in January, June and September. Take a look at our cheap Oconomowoc vacation packages and you could score some great off-season discounts.
How many days is enough for Oconomowoc?
With around 3 days, you'll have plenty of time to experience popular neighborhoods like Summit Corners and Maplewood during your Oconomowoc vacation. Remember to also add Fowler Lake Park and Oakbrook-Eser Studios and Gallery to your list of must-sees. Looking for more adventures? Consider venturing outside of Oconomowoc on tours and day trips.
Is it worth booking a vacation package to Oconomowoc?
Oconomowoc offers everything you need for a wonderful escape. Get your Oconomowoc vacation off to a flying start by visiting top attractions like Oconomowoc Golf Club.
How to find the best Oconomowoc package deals?
Bagging a cheap Oconomowoc package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most affordable Oconomowoc package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book an Oconomowoc vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Oconomowoc vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Oconomowoc?
If you've got your Oconomowoc travel dates confirmed, book early to bag some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Oconomowoc vacation packages?
Your Oconomowoc break is meant to be an escape from your busy life, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
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Things to do in and around Oconomowoc
Oconomowoc, Wisconsin, is perfect for outdoor and romantic getaways, featuring scenic landscapes and a variety of activities. Enjoy recreational areas and golf courses, or participate in community events like fun outdoor festivities, family festivals, and lawn parties. Whether you're looking to relax or engage in lively events, Oconomowoc offers a charming experience for all visitors.
Shopping
For shopping in Oconomowoc, explore local boutiques and shops for unique gifts. If you're up for a drive, visit Johnson Creek Premium Outlets, 13 miles away, or Brookfield Square Mall, 20 miles away, both offering a variety of stores and entertainment options.
Recreation
The Oconomowoc Golf Club offers a tranquil golfing experience surrounded by lush landscapes, perfect for sports enthusiasts. Imagination Station provides a family-friendly playground with outdoor fun for all ages. For a touch of luxury, relax at Pewaukee Lake Beach, where you can enjoy beautiful views and serene surroundings.
Adventure
Experience thrills at Springs Water Park, 12 miles from Oconomowoc, with exciting water slides and family fun. Visit Sussex Bowl, 13 miles away, for arcade adventures and bowling excitement. In winter, hit the slopes at Heiliger Huegel Ski Club, 14 miles away, for skiing and sports enjoyment.
Nightlife
Oconomowoc's nightlife is vibrant, featuring cozy bars and live music venues. Visit the Oconomowoc Arts Center for performances or unwind at The Silver Lake Lounge for drinks and a friendly atmosphere. For a lively evening, check out the local breweries and enjoy craft beers with friends.
Find the best attractions in and around Oconomowoc
Oconomowoc, Wisconsin, offers a delightful mix of outdoor adventures and romantic scenery, making it perfect for travelers seeking culture and family experiences. Explore urban parks, picturesque lakes, and local churches, while also enjoying attractions like the Oconomowoc Arts Center and the Oconomowoc Area Historical Society. Don't miss out on festive Christmas music and learn about the rich history of Oconomowoc during your visit.
- Fowler Lake Park: This urban park in Oconomowoc offers a serene escape with its scenic lake views, walking trails, and picnic areas. Families can enjoy playgrounds, while outdoor enthusiasts can partake in recreational activities, all surrounded by vibrant city vibes.
- Oconomowoc Historical Museum: Immerse yourself in local culture at this history museum, where you can explore exhibits showcasing the rich heritage of Oconomowoc. It’s a great place to learn about the area's past through engaging displays and artifacts.
- Pewaukee Lake: Located 11 miles from Oconomowoc, Pewaukee Lake boasts beautiful beaches and stunning scenery. Perfect for outdoor activities, it also offers a romantic setting, ideal for couples looking to enjoy a peaceful day by the water.
Best time to go to Oconomowoc
The best time to visit Oconomowoc is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with no rain.
Tips to save on your trip to Oconomowoc
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Oconomowoc.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.