Oak Hill Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oak Hill vacation rentals

Waterfront Lake Cottage - Upper Nemahbin Lake

Waterfront Lake Cottage - Upper Nemahbin Lake
Peninsular Park
9.6 out of 10, Exceptional, (30 reviews)
"Our stay couldn’t have been better! Gorgeous place on the water. Hosts were super helpful and accommodating."
United States
Erin M.
The price is CA $690
CA $1,412 total
includes taxes & fees
Jun 10 - Jun 11
Waterfront Lake Cottage - Upper Nemahbin Lake

Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.6 out of 10, Exceptional, (9 reviews)
"Great area!"
United States
Chanel D.
The price is CA $189
CA $332 total
includes taxes & fees
Jun 8 - Jun 9
Historic Downtown Luxury-Lake-Coffee-Spa like BA

Spacious Accessible Studio w/ Walk-In Shower

Spacious Accessible Studio w/ Walk-In Shower
Oconomowoc
The price is CA $170
CA $224 total
includes taxes & fees
Jun 14 - Jun 15
Spacious Accessible Studio w/ Walk-In Shower

Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.6 out of 10, Exceptional, (7 reviews)
"Comfortable, clean, convenient location and stylish decor. Owner was great! Will recommend to my friends."
United States
Susan D.
The price is CA $435
CA $664 total
includes taxes & fees
Jul 8 - Jul 9
Historic Downtown- King Bed-St Johns Acad-Shopping

Private Hot Tub • Bright Home Near Downtown

Private Hot Tub • Bright Home Near Downtown
Oconomowoc
10.0 out of 10, Exceptional, (5 reviews)
"Our stay was wonderful. Our host was very responsive to questions, and the home was welcoming and had all needed amenities. "
United States
Heather F.
The price is CA $240
CA $464 total
includes taxes & fees
Jun 10 - Jun 11
Private Hot Tub • Bright Home Near Downtown

Downtown Lake Country Oconomowoc with River View

Downtown Lake Country Oconomowoc with River View
Oconomowoc
9.8 out of 10, Exceptional, (7 reviews)
"Great location. Host was very responsive. "
United States
Stephen R.
The price is CA $365
CA $576 total
includes taxes & fees
Jun 14 - Jun 15
Downtown Lake Country Oconomowoc with River View

Stylish Retreat by Downtown, Wedding Venues & Lakes + Cozy Fire Pit

Stylish Retreat by Downtown, Wedding Venues & Lakes + Cozy Fire Pit
Oconomowoc
10.0 out of 10, Exceptional, (25 reviews)
"Incredible stay in such a beautiful home! "
United States
Saarah B.
The price is CA $659
CA $1,147 total
includes taxes & fees
Jun 24 - Jun 25
Stylish Retreat by Downtown, Wedding Venues & Lakes + Cozy Fire Pit

Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.8 out of 10, Exceptional, (6 reviews)
"Clean place. "
United States
John M.
The price is CA $275
CA $382 total
includes taxes & fees
Jun 26 - Jun 27
Relax & Reboot in this Charming 2-Bedroom Townhome

The Lodge - Camp Kettlewood

The Lodge - Camp Kettlewood
East Troy
The Lodge - Camp Kettlewood

Dome House on Whitewater Lake

Dome House on Whitewater Lake
Whitewater
10.0 out of 10, Exceptional, (1 review)
"Very quiet, clean and lots of amenities! We had a hiccup with the water/shower, and our host not only communicated quickly but had a plumber over to fix it before the day was over!! She went above and beyond to make our stay comfortable!! A very enjoyable stay!"
United States
Rachel
The price is CA $580
CA $935 total
includes taxes & fees
Jul 6 - Jul 7
Dome House on Whitewater Lake

Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
Elkhorn
9.6 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay, great location and back yard"
United States
Jon L.
The price is CA $532
CA $1,167 total
includes taxes & fees
Jun 8 - Jun 9
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

Queen Studio Suite w/ Kitchenette in Oconomowoc

Queen Studio Suite w/ Kitchenette in Oconomowoc
Oconomowoc
The price is CA $170
CA $224 total
includes taxes & fees
Jun 14 - Jun 15
Queen Studio Suite w/ Kitchenette in Oconomowoc

Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (5 reviews)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is CA $236
CA $411 total
includes taxes & fees
Jun 8 - Jun 9
Historic Downtown-Old World Charm-Dining-Coffee

Accessible 1-BR Suite w/ Two Double Beds

Accessible 1-BR Suite w/ Two Double Beds
Oconomowoc
The price is CA $246
CA $317 total
includes taxes & fees
Jun 14 - Jun 15
Accessible 1-BR Suite w/ Two Double Beds

Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast
Oconomowoc
The price is CA $315
CA $407 total
includes taxes & fees
Jun 9 - Jun 10
Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

2-BR Suite w/ King & Double Beds + Kitchen

2-BR Suite w/ King & Double Beds + Kitchen
Oconomowoc
The price is CA $309
CA $400 total
includes taxes & fees
Jun 21 - Jun 22
2-BR Suite w/ King & Double Beds + Kitchen
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oak Hill Hotel Reviews

Find out more about Oak Hill

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oak Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Oak Hill?

Yes, we have vacation rentals near top attractions in Oak Hill, or you can select a more secluded option if you'd like a relaxing place to stay.

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

Luxury Lakefront Home w Miles of Lake Views, private pier, lake toys & game room: This vacation home rental near Oak Hill is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Family Camp Beach. Old World Wisconsin and University of Wisconsin-Whitewater are a couple of places you'll find in the larger area.

What’s a vacation rental in Oak Hill like?

Vacation rentals are privately owned properties you can book for a long or short time in Oak Hill. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.