Oak Hill Holiday Rentals

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Holiday Rentals in Oak Hill

The Boat House on Pewaukee Lake| Location, Comfort, Experience

10.0 out of 10, Exceptional, (4)
"We are Pewaukee residents and known about the “boat house”for years. When we found it was available thru VRBO, we jumped on it. We had family from Texas visiting for a long week end, we reserved the boathouse. I can sum up there view of the house as fantastic. Not only was it unique, it was clean and fully equipped for their stay. Will definitely sign up for another stay."
The Boat House on Pewaukee Lake| Location, Comfort, Experience

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

10.0 out of 10, Exceptional, (49)
"If we could give 11 stars, we would! Every attention to detail was thought of. The hosts even dropped off an amazing charcuterie board on our arrival. We loved the themed rooms and historical information throughout the house. Would love to stay here again in the summer when we can take advantage of the location on the water. Our young adults loved the Eagle’s Nest and what a beautiful view!"
Waterfront Getaway: Kayaks, fishing, game room, fire pit, gathering room…

Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room

10.0 out of 10, Exceptional, (42)
"The home was beautiful, clean and a joy call our place for a few days. The game room a hit for all and the views over the lake wonderful. The master bedroom and bathroom were filled with little surprises that were delightful. Our 2 1/2 year grandson had fun watching the birds come eat out of the feeder attached to the window. I highly recommend this home. "
Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room

Silos view ranch

10.0 out of 10, Exceptional, (16)
"My husband and go on an annual Fall trip with other couples from a small group from our church. This year we stayed at Silos View and absolutely loved it! The property was fabulous and the host provided a lot of lot of extras, such as snacks and luxury soaps and shampoo. There were many amenities at this home. Our favorite things about this home were the king size beds,updated bathrooms with heated floors and the amazing outdoor living space. We would definitely stay here again!"
Silos view ranch

Beautiful Family Home on Quiet Lake Ashippun

10.0 out of 10, Exceptional, (12)
"We got together to celebrate one of our siblings birthday. My family is from all over and four flew into Milwaukee airport. It was a convenient location to do this. House is beautiful and roomy. Had 6 adults staying and all were comfortable and had plenty of space. We hosted our sibs party and all had a great time and were impressed with the house. Would recommend this property."
Beautiful Family Home on Quiet Lake Ashippun

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

10.0 out of 10, Exceptional, (15)
"Really great location. Excellent accommodation. Clean very well equipped easy check in and out process. Only recommendation a few more blankets for beds. I’m from Fl and was in the teens needed a few extra lol. Thank you for a great home like atmosphere we were in town for our best friends funeral. "
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews

Waterfront on Pewaukee Lake |3BR/2BA|Private Pier

Waterfront on Pewaukee Lake |3BR/2BA|Private Pier

Greenstone Cottage

10.0 out of 10, Exceptional, (16)
"Loved the property . Would recommend "
Greenstone Cottage

Beautiful Historic Tudor Mansion with sandy Private Beach

9.6 out of 10, Exceptional, (30)
"We had a big crew that loves to play pickleball, jump in the pool, and blow some steam off in the sauna after an active day at the house that has it all!"
Beautiful Historic Tudor Mansion with sandy Private Beach

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.

NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

9.8 out of 10, Exceptional, (9)
"We had multiple generations coming from many locations to celebrate mom’s 80 birthday. This home was large enough to accommodate all 13 for meals and gatherings very comfortably. There were spaces people could chat privately and a great room for everyone! Eleven of us slept there. We would definitely come again. "
NEW Sunset Lake House w/ 4 fireplaces and kids bunk room!

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

9.8 out of 10, Exceptional, (8)
"Each year our extended family meets in Wisconsin for Christmas. This year we chose to find a location closer to Milwaukee. This recently restored Victorian worked well for our family. 8 of stayed at the house, while 8 others visited during the day. Plenty of room for the family to meet. Large kitchen and dining area. Plenty of places to park. Beautiful neighborhood. Jay our host was readily accessible and responsive prior to our visit, and we found the house very accommodating. "
Magnificently restored, charming, 8+ Bed-Victorian on a beautiful 1.5 acres.

Beautiful Waukesha Home

10.0 out of 10, Exceptional, (25)
"The house was awesome , nice neighborhood great view from kitchen. easy to get around the city. perfect place to call home while we were there. "
Beautiful Waukesha Home

Four Gables on Green Lake- Luxury Lakefront Home w/Water Views from Every Room!

Four Gables on Green Lake- Luxury Lakefront Home w/Water Views from Every Room!

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

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!

comfortably sleeps 10 guests

10.0 out of 10, Exceptional, (31)
"We had everything we needed and more in a good location. Great host, great communication. "
The price is AU$680
includes taxes & fees
18 Feb - 19 Feb
comfortably sleeps 10 guests

Nagawicka Woods-Beautiful Lake Country Ranch Home

10.0 out of 10, Exceptional, (72)
"Our group really enjoyed staying here for the weekend! Host was very nice, the place was clean and well kept. Would definitely stay here again!"
Nagawicka Woods-Beautiful Lake Country Ranch Home

Delavan Retreat w/ Patio on Turtle Lake!

10.0 out of 10, Exceptional, (7)
"We had an amazing stay at this cabin! The place was exactly as advertised—perfect for a relaxing lake getaway. It was spotless and beautifully decorated, making it feel cozy and inviting. The location couldn’t have been better, with easy access to the lake and surrounding areas. Communication with the host was seamless, and we had no issues checking in or out. Overall, a fantastic experience, and we would definitely stay here again! "
Delavan Retreat w/ Patio on Turtle Lake!

Cozy Delafield Apartment - Walk to Lake!

9.8 out of 10, Exceptional, (8)
"Clean, had everything that one would expect in a fun weekend get away! There were 4 adults staying. 2 bedrooms, 1 bath and a living space with a small kitchen and living room configuration. Beautifully decorated! Snacks were provided, which was a nice surprise! Cute shops and nice dining experiences. "
Cozy Delafield Apartment - Walk to Lake!
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 Oak Hill you may be interested in

The Ingleside Hotel

4.0 star property
8.6 out of 10, Excellent, (593)
"The staff was friendly and the food at the supper club was excellent."
The price is AU$191
includes taxes & fees
3 Mar - 4 Mar
The Ingleside Hotel

Holiday Inn Express & Suites Delafield by IHG

2.5 star property
9.4 out of 10, Exceptional, (493)
"Close to shopping and dining."
The price is AU$183
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Express & Suites Delafield by IHG

La Quinta Inn & Suites by Wyndham Milwaukee Delafield

2.5 star property
8.6 out of 10, Excellent, (1004)
"I would stay here again"
The price is AU$136
includes taxes & fees
19 Feb - 20 Feb
La Quinta Inn & Suites by Wyndham Milwaukee Delafield
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.

Frequently asked questions

Can I find holiday rentals in Oak Hill?

Yes, there are holiday rentals close to the most popular sights in Oak Hill, or you can select a more secluded option if you're looking for a relaxing stay.

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

Four Gables on Green Lake- Luxury Lakefront Home w/Water Views from Every Room!: This holiday home rental outside of Oak Hill is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Oak Hill?

Explore the area and family-friendly sights such as Kettle Moraine Ranch, or get out into nature at a spot like Green Lake. Old World Wisconsin and University of Wisconsin-Whitewater are a couple of places you'll find in the wider area.

What’s a holiday rental in Oak Hill like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oak Hill. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.