Holiday Homes in Oconomowoc

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Featured Holiday Homes in Oconomowoc

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

10.0 out of 10, Exceptional, (321)
"Great house for being in the lake. Has a nice backyard that is fenced in and was perfect for our dogs. "
Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River

Amazing Five Bedroom Milwaukee Vacation Home!!

10.0 out of 10, Exceptional, (37)
"Went for our annual golf trip. Perfect house for the 6 of us. Never had to leave the house after our rounds!"
Amazing Five Bedroom Milwaukee Vacation Home!!

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

9.8 out of 10, Exceptional, (62)
"Property owner was great to deal with, and communication was also very good. The neighborhood was quiet, and there is a nice bar/restaurant directly next door. All amenties were exactly as described."
Cottage On The Canal - An All Seasons Getaway - Waterford - Lake Tichigan

4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

9.6 out of 10, Exceptional, (157)
"Enjoyed being close to the wedding venue. Samantha was available to answer any questions. The bedrooms were large and living space great for family. "
4BR House in Glacier Hills County Park / Heart of the Kettle Moraine!

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (21)
"Beautiful home in a quiet neighborhood. Very clean property with all the amenities needed for our son’s wedding weekend. Host was very responsive and accommodating. Would definitely stay again if in the area. "
The price is AU$849
includes taxes & fees
24 Nov - 25 Nov
Beautiful Waukesha Home

Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

10.0 out of 10, Exceptional, (5)
"The place was great. Beautiful location. Relaxing environment. Convenience amenities. We really enjoyed the kayaks and the fire pit. Gorgeous sunrises and sunsets. Would highly recommend!"
The price is AU$563
includes taxes & fees
24 Nov - 25 Nov
Tichigan Lake House - Pontoon Boat & Fire Pit - Dog Friendly - Newly Renovated

Beautiful lakefront, Newly Remodeled Lower Level!

9.8 out of 10, Exceptional, (173)
"We had a wonderful stay; only complaint was that we couldn't get the outside light to work in the back, by the hot tub. Would definitely come again!"
Beautiful lakefront, Newly Remodeled Lower Level!

Spacious Pewaukee Lake/ Pier Access Home

8.6 out of 10, Excellent, (11)
"Our company needed to send workers out of town to a job site in the Delafield area. The house was perfect for our needs, close to the job site and enough beds for each person. That is always our struggle, enough beds, they will share a room but not a bed. Our employees enjoyed being able to sit out after a long day and sit around the fire pit and relax. Steve was great to work with, as we needed to book an additional week and despite having availability VRBO site showed it unavailable. We...
Spacious Pewaukee Lake/ Pier Access Home

Historic, Vintage, Classy, 11 bed, 5+ bath!

10.0 out of 10, Exceptional, (6)
" We were immediately impressed with the property! It was beautiful and well appointed.The host was responsive."
Historic, Vintage, Classy, 11 bed, 5+ bath!

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

10.0 out of 10, Exceptional, (31)
"We loved our stay here. We wanted a quiet place to stay for an extended weekend and this was the perfect spot. My kids loved the pier, the kayaks, and the bikes. I loved the giant couch and the view! The pictures didn't show off how amazing this house really is so when I walked in I literally said "Wow!". The house had everything you could possibly need. Thank you for letting us stay at your property. We will definitely be back again. "
Family Friendly Sandy Beach Lake Home! Your 3Bed, 2Bath Escape For All Seasons!

Cozy, private, cabin on a quiet lake.

9.8 out of 10, Exceptional, (60)
"Great first trip out. Hoping to come back when it’s warmer out to enjoy the lake more. "
Cozy, private, cabin on a quiet lake.

🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

9.6 out of 10, Exceptional, (10)
"Lovely unit very clean, and great hosts!"
🌊 Well Appointed Home Steps from Pewaukee Lake + KING Bed 🌊

Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

10.0 out of 10, Exceptional, (22)
"Pleasant stay at a comfortable home. Thank you. "
Pewaukee Lake Home: Sunsets, Dogs & Good Vibes

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (11)
"This was our 2nd stay at this property within 3 months and it was equally as great as the first. Michael & Angie are wonderful hosts and we’re looking forward to renting their home again in 2025."
Beautiful Family Home on Quiet Lake Ashippun

W172-Center-1 · Lake Muskego House, Walk to Stores & Restaurants

10.0 out of 10, Exceptional, (10)
"Perfect in every way! Clean, functional and convenient to stores and restaurants while still feeling the lake vibe! We loved it!"
The price is AU$351
includes taxes & fees
19 Dec - 20 Dec
W172-Center-1 · Lake Muskego House, Walk to Stores & Restaurants

Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

10.0 out of 10, Exceptional, (7)
"Great property right on Lauderdale Lakes and next door to Lauderdale landing. House was new, clean, and great for entertaining a large group. Briana was a fantastic host with lightning-quick responses. Couldn't recommend this property enough for larger groups looking to spend a few days on the lake."
Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!

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

10.0 out of 10, Exceptional, (99)
"One of the most beautiful homes in Wisconsin, cherished each night spend here. "
Spectacular 77 acre estate, fishing ponds & close to Kettle Moraine trails

W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

9.6 out of 10, Exceptional, (5)
"Home needs a few fixes, but easy to do. Overall good property . Convenient placement with lots to do and many restaurants and convenient stores for provisions. "
The price is AU$429
includes taxes & fees
3 Dec - 4 Dec
W172-Lannon · Charming Muskego House, Walk to Lake & Restaurants

The Beverly on Buena Lake-Hot tub, Kayaks, Ice Fishing

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay . "
The Beverly on Buena Lake-Hot tub, Kayaks, Ice Fishing

Spacious, Upscale Whitewater Lake Home |200+ Ft of Lake Frontage |Swim Deck |Docks |Screened Porch

10.0 out of 10, Exceptional, (3)
"The house was beautiful and comfortable. We had a great long weekend away. Would definitely return in the future! "
Spacious, Upscale Whitewater Lake Home |200+ Ft of Lake Frontage |Swim Deck |Docks |Screened Porch
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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Other property types in Oconomowoc

3 Bedroom Okauchee Lake

9.2 out of 10, Wonderful, (10)
"Property description is accurate, yes you are staying above a very popular bar so you will hear the music late into the evening. We were there for a holiday weekend so this was just fine for us and our adult kids! Hosts communicated promptly and even provided a waffle bar and snacks! Loved being able to go downstairs and order food and drinks. We also walked to nearby restaurants, a perfect location to experience some lake life. Thank you!"
3 Bedroom Okauchee Lake

Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

10.0 out of 10, Exceptional, (30)
"The house was beautiful. Well equipped and comfortable. Had a few elderly individual staying at the home, they were just a little scared of the stairs. (narrow stairs and curvy). Great location to the function all had to attend. Close to town and walkable. I would gladly use this VRBO again I loved the home!"
Exquisite Newly Renovated Historic Lake Country Home - Maison La Belle

Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

10.0 out of 10, Exceptional, (14)
"Our family had a fun stay at this property. Many amenities and a great location. Thank you!!"
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
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.
Beautiful view of the beach with palm trees

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