Oconomowoc Holiday Rentals

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Holiday Rentals 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
Waterfront Lake Cottage - Upper Nemahbin Lake
9.6 out of 10, Exceptional, (25)
"Property manager very helpful and prompt. Great location for us. Nice lakeshore. Low ceilings so tall people beware. Note: no potable water but they provide drinking water. This property more like rustic cabin rental. Also need to be very careful walking down uneven steps down to front door so not for elderly."
Waterfront Lake Cottage - Upper Nemahbin Lake
✨ Chic Retreat with King Bed near Wedding Venues, Downtown + Lakes ✨
10.0 out of 10, Exceptional, (9)
"The home was exactly how it looks. Online was very clean, beautifully decorated. The furnishings are comfortable. There are so many details to the amenities that just makes this the perfect stay."
✨ Chic Retreat with King Bed near Wedding Venues, Downtown + Lakes ✨
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
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!!
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!
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
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
Private estate with tennis court and more
10.0 out of 10, Exceptional, (38)
"We rented for a golf weekend! Close to Washington County course, Erin Hills and the Bog. Played Brown Deer on the way up. Property was everything needed and beautiful grounds! Would stay again!"
Private estate with tennis court and more
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
10.0 out of 10, Exceptional, (5)
"Beautiful home and property, lots of space to spread out and have privacy. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
9.8 out of 10, Exceptional, (90)
"Relaxing weekend with a mom and daughter, and daughter-in-law. We were looking for a relaxing weekend with reading, good eating and drinking and nearby small town shops. And we got it all. 1bedroom downstairs, large Master on the main floor. A lot of spaces to relax, the property is gorgeous. The kitchen is impressive. Communication was easy, quick and helpful."
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
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!
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
8.6 out of 10, Excellent, (11)
"Enjoyed the spaces for young adults and parents to hang out together and separately. Had a fantastic time at the cabin and enjoyed the lake access for water sports."
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
Fall Deals! - Mins to Froedert/State Fair - Dogs!
9.6 out of 10, Exceptional, (8)
"Our family of 6 older adults (48-71) were in town for a funeral. CUTE home 20 minutes from everything we had to attend. Close to the interstate. Easy booking, quick response from the owner/host. The patio was a great gathering place as we had very comfortable weather. Mr. Ackley promptly addressed an issue that arised after hours on a Friday!!! That is a great host! Give this cozy home a try!"
Fall Deals! - Mins to Froedert/State Fair - Dogs!
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
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!
🌊 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 🌊
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
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 types of properties in Oconomowoc you may be interested in

Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel
3.0 star property
9.0 out of 10, Wonderful, (680)
"Love Staybridge Suites as there's always great staff service, nice, clean, spacious room with many kitchen items which is great for cooking or warming up! The breakfast is terrific with hot entrees, oatmeal, toast, fruit, yogurt, hot teas, coffee. Cold warer. It's all top notch and we stay every tîme we're in town!"
The price is AU$186
includes taxes & fees
15 Dec - 16 Dec
Staybridge Suites Milwaukee West-Oconomowoc, an IHG Hotel
Hilton Garden Inn Oconomowoc
3.0 star property
9.0 out of 10, Wonderful, (595)
"I had a delightful stay. I have nothing negative to say about my experience."
The price is AU$199
includes taxes & fees
15 Dec - 16 Dec
Hilton Garden Inn Oconomowoc
TownePlace Suites by Marriott Oconomowoc
2.5 star property
9.0 out of 10, Wonderful, (76)
"Its a safe and quiet place to stay"
The price is AU$194
includes taxes & fees
22 Dec - 23 Dec
TownePlace Suites by Marriott 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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Oconomowoc?

Yes, there are holiday rentals in Oconomowoc close to Fowler Lake Park, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Oconomowoc. Make sure you have time to check out the cafés and sporting events during your trip.

What are some of the best holiday rentals that Oconomowoc has to offer?

Relaxing Waterfront Home on Elm Island Great Fishing on Lake Tichigan/Fox River: This holiday home rental outside of Oconomowoc is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals are there in Oconomowoc?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your Oconomowoc stay.

What’s there to see and do in Oconomowoc?

Enjoy the outdoors at Lac La Belle and Fowler Lake Park, or simply take in cultural attractions like Theatre On Main and Oconomowoc Gallery. Other places in town to visit include Oakbrook-Eser Studios and Gallery and Oconomowoc Historical Museum.

What’s a holiday rental in Oconomowoc like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oconomowoc. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.