Holiday Homes in Oconomowoc

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Oconomowoc and around

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby
Terrace/patio

NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby

10.0 out of 10, Exceptional, (4)
"Beautiful home with beautiful surroundings. Beautiful home great place to stay."
NEW! Experience the Serene & Unique Blue Tree House – Hike, Relax & Lake Nearby
Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails
Outdoor pool, a heated pool

Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails

10.0 out of 10, Exceptional, (103)
"One of the most beautiful homes in Wisconsin, cherished each night spend here. "
Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails
4 Bdrm 4 Bath Lake front Lake Sinissippi home
Outdoor dining

4 Bdrm 4 Bath Lake front Lake Sinissippi home

10.0 out of 10, Exceptional, (42)
"Myself and a group of friends stayed at Chase's home in August and we had such a great time. The house was spacious enough for all of us to be together. The weather was fantastic so we got to use the different outdoor toys and hangout in the water a lot too. Nice and private area where we felt comfortable to do as we pleased. We would definitely come back again!"
4 Bdrm 4 Bath Lake front Lake Sinissippi home
Family And Pet-Friendly On Waubeesee Lake ~ Includes Kayaks!
Property grounds

Family And Pet-Friendly On Waubeesee Lake ~ Includes Kayaks!

9.8 out of 10, Exceptional, (98)
"The location was perfect and beautiful. We can't wait to come back during the summer so we can enjoy the lake! "
Family And Pet-Friendly On Waubeesee Lake ~ Includes Kayaks!
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Fridge, microwave, oven, stovetop

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

9.8 out of 10, Exceptional, (353)
"This Elm Island home was perfect for our 6 adults and 4 toddlers. The living area was roomy with enough seating to accommodate our group. Kitchen had lots of counter space, and backyard was fenced to corral the dog. Would definitely stay again if in the area. "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River
Beautiful Family Home on Quiet Lake Ashippun
Interior

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (22)
"Excellent place to stay, just as described, great neighborhood."
Beautiful Family Home on Quiet Lake Ashippun
Historic Brookfield Farm Home ~ 14 Mi to Milwaukee
Terrace/patio

Historic Brookfield Farm Home ~ 14 Mi to Milwaukee

9.4 out of 10, Exceptional, (18)
"The farmhouse was so charming! We had a great experience!"
Historic Brookfield Farm Home ~ 14 Mi to Milwaukee
LAKEFRONT HIDDEN GEM !
Balcony

LAKEFRONT HIDDEN GEM !

9.6 out of 10, Exceptional, (35)
"Greatly enjoyed our time here."
LAKEFRONT HIDDEN GEM !
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!
Beach nearby, sun-loungers, beach towels

Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

10.0 out of 10, Exceptional, (32)
"Loved everything and can't wait to come back again!"
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Outdoor dining

Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

9.8 out of 10, Exceptional, (13)
"The house was amazing. The kitchen was fabulous. There was spices and supplies, even though we werent ther but during the night. Plenty of space, clean and beautiful. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Lauderdale Lakes Stay: Seasonal Hot Tub & Firepit
Fridge, microwave, oven, stovetop

Lauderdale Lakes Stay: Seasonal Hot Tub & Firepit

9.2 out of 10, Wonderful, (5)
"This house is very nice and large! The owners have provided a great restful place. The beds are comfy and they are not stingy with towels and toiletries. The basement was a great addition. The owners were also great with communication. We were very disappointed we couldn't use the fireplace or the hot tub, but still enjoyed our stay."
Lauderdale Lakes Stay: Seasonal Hot Tub & Firepit
Linda's Lookout - Country Charm
Interior

Linda's Lookout - Country Charm

Linda's Lookout - Country Charm
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle
Dining

Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle

10.0 out of 10, Exceptional, (2)
"Katie was the most welcoming host you can ask for. She was really sweet and the home was just breathtaking. Lots of space, big kitchen, and plenty of activities to pass time with. We were a group of 10 adult men celebrating for a bachelor party and we did not regret the house we selected. The lake activities really sell the experience. You have kayaks and then there's the boat tubing! Make sure you ask about that and schedule a time with Katie to take you out on the boat. We even got to see a...
Kohl Manor Luxury Lake 8-br exclusive retreat Pool, Cinema, Arcade on LacLaBelle
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Fridge, microwave, oven, stovetop

Wooded Hills/Indoor Pool/Hot Tub/Arcade

9.8 out of 10, Exceptional, (47)
"House was clean and spacious. Pool and extra amenities were great!"
Wooded Hills/Indoor Pool/Hot Tub/Arcade
Unique Family Home Overlooking Beautiful Wind Lake With 117' Lake Frontage
Exterior

Unique Family Home Overlooking Beautiful Wind Lake With 117' Lake Frontage

9.6 out of 10, Exceptional, (119)
"The best place ever we will come back soon 🙂"
Unique Family Home Overlooking Beautiful Wind Lake With 117' Lake Frontage
Spacious 4-bedroom house in terrific Menomonee Falls with WiFi, AC
Fridge, microwave, oven, stovetop

Spacious 4-bedroom house in terrific Menomonee Falls with WiFi, AC

9.4 out of 10, Exceptional, (14)
"The host was very very nice with us quick response time extremely clean property I’d definitely book here again"
The price is €338
includes taxes & fees
18 Aug - 19 Aug
Spacious 4-bedroom house in terrific Menomonee Falls with WiFi, AC
Farmhouse with Heated Pool on almost 160 Acres!
Fridge, microwave, oven, stovetop

Farmhouse with Heated Pool on almost 160 Acres!

9.8 out of 10, Exceptional, (6)
"Kevin was wonderful, the house & property was perfect. Can’t wait to come back."
Farmhouse with Heated Pool on almost 160 Acres!
Waterfront Getaway: Kayaks, fishing, game room, fire pit, gathering room…
Terrace/patio

Waterfront Getaway: Kayaks, fishing, game room, fire pit, gathering room…

10.0 out of 10, Exceptional, (56)
"This is a spectacular property. The host do an incredible job making sure you have everything you could possibly need to have a great stay"
Waterfront Getaway: Kayaks, fishing, game room, fire pit, gathering room…
💫 Luxury Lakeview Getaway: Main & Guest House, Sleeps 10 💫
Fridge, microwave, oven, stovetop

💫 Luxury Lakeview Getaway: Main & Guest House, Sleeps 10 💫

10.0 out of 10, Exceptional, (5)
"Our family from around Wisconsin gathered at this house to celebrate the holidays. It was a beautiful space with all the amenities needed to make meals and enjoy each other's company. The view of Pewaukee Lake is breathtaking and made the house extra special. I hope we can visit again soon."
💫 Luxury Lakeview Getaway: Main & Guest House, Sleeps 10 💫
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan
Property grounds

Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

9.8 out of 10, Exceptional, (66)
"Good location, great host, nice break!"
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan
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.
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Top Oconomowoc Hotel Reviews

Renaissance Milwaukee West Hotel

Renaissance Milwaukee West Hotel

10/10 Excellent
"The staff here made my stay enjoyable. Parking was easy to find and I felt safe coming and going. I had.breakfast there daily and the food was fantastic. This my new go to place . "
ava 3-night trip
Posted 17 hours ago
Renaissance Milwaukee West Hotel