Oconomowoc Vacation Packages 2026 from $340

Your Oconomowoc Vacation

Say goodbye to the hassle of planning and hello to a Oconomowoc vacation package. With the finer details organized before you go, you can focus on discovering this city, starting with Halls Park, which is good for nature, watersports and views. If a sightseeing tour is part of the plan during your trip to Oconomowoc, look around top attractions like Fowler Lake Park, Oconomowoc Arts Center and Oconomowoc Golf Club. Stop dreaming and start doing. Check out the broad range of options on Expedia today and finally put your Oconomowoc vacation plans into action!

The Latest Oconomowoc vacation packages

Price found within the past 48 hours. Click for updated prices.

Sheraton Milwaukee Brookfield Hotel

$340

per person

Mar 6 - Mar 8

found 24 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

8.4/10 Very Good! (500 reviews)

Wonderful stay, clean room, friendly staff, lots of shopping near by

Reviewed on Jan 9, 2026

The Delafield Hotel

$448

per person

Mar 6 - Mar 8

found 24 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

9.6/10 Exceptional! (425 reviews)

The room was big, but pretty cold. The dinner at I.D. was good. There was no breakfast included.

Reviewed on Jan 6, 2026

Hampton Inn & Suites Milwaukee Downtown

Westown

$490

per person

Mar 6 - Mar 8

found 24 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Milwaukee (MKE)

6.6/10 (1,003 reviews)

The front desk staff for the counter was excellent at check-in, check-in and in the evening. They were courteous, and helped us with towels and restaurant recommendations. The maintenance person during the day was also very helpful. The issues with the small store at the front and the rooms are the big reason I would not stay again. The front store area is understocked, and needs meds, toiletries, diet soda, other diet drinks, energy drinks and regular drinks. The 4th floor rooms both looked old, and had an odor. We had to spray both rooms with Febreze from the desk. Both rooms were way too warm, and the ceiling/wall mounted unit did not work well. Maintenance came up and tried to get them working, but the rooms stayed too warm, in the upper 70’s, throughout. Our room on the 6th floor had a better system mounted on the wall, and that worked well. The room also smelled better, and appeared to be newer. Another issue is that only one of our three rooms had a microwave, albeit way too small and not powerful enough, and the other 4th floor rooms had refrigerators that were too small, and no microwave or cups. My granddaughters found a crack pipe in one of the 4th floor rooms, in the closet. We turned it in at the desk. The pool and hot tub were nice, but both the pool area and the rooms have way too few towels. We had to get more from the desk for both areas, and the pool was not busy. The 4th floor rooms had broken bathroom door locks and loose toilet paper holders.

Reviewed on Jan 11, 2026

Kinn Guesthouse Bay View

Bay View

$630

per person

Mar 29 - Apr 4

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Milwaukee (MKE)

9.6/10 Exceptional! (428 reviews)

The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

Saint Kate - The Arts Hotel

Downtown Milwaukee

$725

per person

Mar 29 - Apr 4

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Milwaukee (MKE)

9.8/10 Exceptional! (2,425 reviews)

Rooms are clean , valet parking is terrible. Many times I almost had to valet my car on my own ,because nobody was there to assist

Reviewed on Jan 12, 2026

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Where to stay in Oconomowoc

Find the best Oconomowoc areas and neighborhoods for the activities you enjoy most. Learn more about 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 Fowler Lake Park.

Discover the most popular places to visit in Oconomowoc

Fowler Lake Park

Explore the great outdoors at Fowler Lake Park, a lovely green space in Oconomowoc. Visit the shops or attend a sporting event in this family-friendly area.

Oconomowoc Historical Museum

You can spend time browsing the exhibits at Oconomowoc Historical Museum in Oconomowoc. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Golf Club

Enjoy a round of golf in Oconomowoc at Oconomowoc Golf Club. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Hotel Deals

Staybridge Suites Milwaukee West-Oconomowoc by IHG

1141 Blue Ribbon Drive Oconomowoc WI

Fully refundable

$99 nightly

$112 total

Feb 1 - Feb 2

Total with taxes and fees

9/10 Wonderful! (837 reviews)

Staff was great! Was disappointed that there was no restaurant in the hotel. When we book the description said there was one but were told that was their sister company across the street. Very disappointed as i’m in my upper 60’s and don’t like to go out at night. Pool area had grit and tiny little ...

Reviewed on Jan 6, 2026

TownePlace Suites by Marriott Oconomowoc

1242 CORPORATE CENTER DRI Oconomowoc WI

Fully refundableReserve now, pay when you stay

$116 nightly

$131 total

Jan 18 - Jan 19

Total with taxes and fees

9.2/10 Wonderful! (156 reviews)

Clean room

Reviewed on Jan 11, 2026

Hilton Garden Inn Oconomowoc

1443 Pabst Farms Cir Oconomowoc WI

Fully refundableReserve now, pay when you stay

$103 nightly

$117 total

Feb 8 - Feb 9

Total with taxes and fees

8.8/10 Excellent! (662 reviews)

Excellent at this price point and location.

Reviewed on Dec 14, 2025

See all 472 properties in Oconomowoc

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Oconomowoc Vacation Packages

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.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	19.8°F (-6.8°C)	No Rain	Mostly Cloudy	Average	Slightly Low
February	21.7°F (-5.7°C)	No Rain	Mostly Cloudy	Average	Slightly Low
March	34.5°F (1.4°C)	Light Rain	Mostly Cloudy	Average	Average
April	44.6°F (7.0°C)	Light Rain	Mostly Cloudy	Slightly High	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	66.7°F (19.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	71.4°F (21.9°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	69.8°F (21.0°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	63.0°F (17.2°C)	Light Rain	Mostly Sunny	Average	Average
October	50.2°F (10.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	37.6°F (3.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	27.5°F (-2.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low

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.

Oconomowoc Essential Information

Language	English
Currency	U.S dollars
Population	16,400
Max Temp Winter	25ºF
Max Temp Summer	75ºF
Top Sights	Oconomowoc Historical Museum, Fowler Lake Park and Oconomowoc Golf Club

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Frequently asked questions

How much does an Oconomowoc vacation package cost?

You'll find cheap prices from $340 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Oconomowoc Vacations from $340

Book a Hotel + Flight or Car together to unlock savings

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Your Oconomowoc Vacation

The Latest Oconomowoc vacation packages

Sheraton Milwaukee Brookfield Hotel

The Delafield Hotel

Hampton Inn & Suites Milwaukee Downtown

Kinn Guesthouse Bay View

Saint Kate - The Arts Hotel

Where to stay in Oconomowoc

Maplewood

Lac La Belle Manor

Peninsular Park

Discover the most popular places to visit in Oconomowoc

Fowler Lake Park

Oconomowoc Historical Museum

Oconomowoc Golf Club

Oconomowoc Hotel Deals

Staybridge Suites Milwaukee West-Oconomowoc by IHG

TownePlace Suites by Marriott Oconomowoc

Hilton Garden Inn Oconomowoc

Find the Best Oconomowoc Vacation Packages

Things to do in and around Oconomowoc

Find the best attractions in and around Oconomowoc

Best time to go to Oconomowoc

Tips to save on your trip to Oconomowoc

Oconomowoc Essential Information

More vacations you might like

Frequently asked questions

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