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Top Holiday Rentals in Oak Hill

SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
9.0 out of 10, Wonderful, 8 reviews
"This is a great location, remote and quiet, just what we wanted. Our family reunion was a big success! No WiFi was an issue for people who needed to make contact with work issues, and of course kids were not happy about it, but sometimes it’s nice to disconnect. However cell phone reception was limited so getting directions was challenging at times. All said and done we had a wonderful time and wouldn’t hesitate to go back and do it again."
SuMMeR IS HeRe BrinG ur boat and tie to dock, Tavern, huge DECK, KIDS jungle gym
Cozy, private, cabin on a quiet lake.
9.8 out of 10, Exceptional, 53 reviews
"Your property was perfect -- clean, well maintained, and ready when promised. All that was needed for the stay was there. Thank you! We plan on returning!!"
Cozy, private, cabin on a quiet lake.
Lakefront Home w/ Gorgeous Sunsets, Kayaks, & Pier
9.8 out of 10, Exceptional, 7 reviews
"This wonderful lake home far exceeded our expectations !!!! Beautifully decorated, extremely inviting and extremely clean….. We will be back !!!"
Lakefront Home w/ Gorgeous Sunsets, Kayaks, & Pier
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Lakefront Access Cottage on Lake Koshkonong
10.0 out of 10, Exceptional, 1 review
"The place was great! Close to Sunset Bar and the town of Fort Atkinson. Would definitely recommend."
Lakefront Access Cottage on Lake Koshkonong
Beautiful Waukesha Home
10.0 out of 10, Exceptional, 7 reviews
"The listing was as depicted. Beautiful home in a very quiet neighborhood. Nice place to relax after seeing the sights. Only thing I missed was having coffee at the ready in the morning."
The price is £438
per night
13 Jun - 14 Jun
Beautiful Waukesha Home
Family Retreat, private, large, great for multi-family, company retreat, wedding
10.0 out of 10, Exceptional, 46 reviews
"This property is fantastic! Great amenities, clean, huge open spaces, and comfortable beds! The owners/property managers were great, too!"
Family Retreat, private, large, great for multi-family, company retreat, wedding
Log Cabin, two mins from Pewaukee Lake Boat Launch
10.0 out of 10, Exceptional, 7 reviews
"We had a great stay at the Hidden Hideaway Cabin. We found everything clean and comfortable and we had everything we needed. We would like to return sometime and would recommend this vacation rental to other couples as well as groups. B&M"
Log Cabin, two mins from Pewaukee Lake Boat Launch
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
10.0 out of 10, Exceptional, 13 reviews
"We thoroughly enjoyed our stay. Great house, perfect view, brilliant location. We thank you so much for the festive decorations and tree! We’ll be back to see you one summer…"
Luxury Lakefront Home, Okauchee Lake's Finest Swim Frontage, 3 levels LakeViews
Delafield Vacation Rental Near Lakes & Parks!
6.0 out of 10, 1 review
"Andrea the host is great but VRBO is a terrible company through which to rent the apartment. VRBO added charges that were not known to her or to me as a guest. This included a very high service fee as well a damaged protection fee. In addition Andrea charges per night were significantly less than what VRBO charged. Our host, Andrea, is trying to get VRBO to refund some of its charges. Unless they agree I will never rent from VRBO again. Renter beware! If you c"
Delafield Vacation Rental Near Lakes & Parks!
Beautiful Family Home on Quiet Lake Ashippun
Beautiful Family Home on Quiet Lake Ashippun
Greenstone Cottage
10.0 out of 10, Exceptional, 7 reviews
"The hostess Carol was great. The home was charming and comfortable - clean and convenient, just a short walk downtown. Definitely would stay again."
Greenstone Cottage
THREE BEDROOM COTTAGE ACROSS FROM NATIONAL HISTORIC LANDMARK AZTALAN MOUNDS
10.0 out of 10, Exceptional, 40 reviews
"We had two daughters graduating on the same day. One at UW Madison and one at Marquette. We stayed here so we could celebrate in both cities and venues. It worked very well logistically."
THREE BEDROOM COTTAGE ACROSS FROM NATIONAL HISTORIC LANDMARK AZTALAN MOUNDS
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
9.8 out of 10, Exceptional, 88 reviews
"Had a great time spending Christmas with my family here, will definitely consider staying again!"
Stunning Log Cabin Getaway Near Lake Beulah *Pool Table*Grill
Silos view ranch
10.0 out of 10, Exceptional, 6 reviews
"We really enjoyed the weekend at Silos View. The property and the house were impeccable. Very clean and cozy decor. So much to do. One of the days was rainy but we still had plenty to do inside. Definitely recommend this property and would love to go back. 5 star review."
Silos view ranch
comfortably sleeps 10 guests
10.0 out of 10, Exceptional, 25 reviews
"Excellent for a small group of people to get away and spend a long weekend knitting, crocheting, spinning and weaving. Spacious enough for everyone. Charming old building with well done updates."
The price is £347
per night
11 Jun - 12 Jun
comfortably sleeps 10 guests
Wooded Pond Retreat
10.0 out of 10, Exceptional, 16 reviews
"This was our second stay at this property in Milton, and it was every bit as good as our first time. The property is well suited for family groups, with three large bedrooms and very comfortable living areas. The kitchen is very well-equipped, with plenty of basic supplies. Kristine is an outstanding host, making us feel very welcome, and providing a very homey environment. Can’t think of a single negative for this property — wholeheartedly recommend it."
Wooded Pond Retreat
Waterfront Lake Cottage - Upper Nemahbin Lake
9.8 out of 10, Exceptional, 23 reviews
"This truly was the best day I have ever experienced while booking a vacation home. The property owners were very polite and more than helpful. If you ever get a chance to go I would highly recommend it. My wife child and myself along with our friends had one of the best weekends we ever did together. The owners truly took time to explain everything and make sure we were comfortable. The house is beautiful everything well-kept. Will definitely be back for another stay!"
The price is £819
per night
11 Jun - 12 Jun
Waterfront Lake Cottage - Upper Nemahbin Lake
Pewaukee Lake House Rental with Pier, 4 Bedrooms 2.5 Baths - Family Friendly
10.0 out of 10, Exceptional, 9 reviews
"Great location. Town is less than a mile away…an easy walk for coffee or more. This home is family friendly with 2 kayaks & 2 kiddie kayaks & all sizes of life vests…on & on. We enjoyed the BBQ grill…The deck overlooking the lake is fab/both main floor deck & walkout basement seating below. Good times!"
Pewaukee Lake House Rental with Pier, 4 Bedrooms 2.5 Baths - Family Friendly
Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!
10.0 out of 10, Exceptional, 1 review
"This home is amazing with great creature comforts and fantastic views. The host (Briana) was quite accommodating. We had a wonderful stay. Everyone enjoyed it. Fishing was slow, but the kids still caught quite a few bass. The nearby hiking trails are spectacular."
Newly remodeled Lauderdale Lakes waterfront home-hot tub, sauna, pickleball!
Luxurious Lake Home - Sleeps 14 - Southeast WI
9.4 out of 10, Exceptional, 3 reviews
"Large, spacious home. Perfect for what we needed."
Luxurious Lake Home - Sleeps 14 - Southeast WI
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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.

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, 457 reviews
"Great place"
The price is £95
per night
24 Jun - 25 Jun
The Ingleside Hotel
Best Western Waukesha Grand
2.5 star property
8.0 out of 10, Very good, 1,007 reviews
"Still didn’t get my security deposit back "
The price is £69
per night
23 Jun - 24 Jun
Best Western Waukesha Grand
La Quinta Inn & Suites by Wyndham Milwaukee Delafield
2.5 star property
8.6 out of 10, Excellent, 1,006 reviews
"Everything is very clean and polite"
The price is £87
per night
11 Jun - 12 Jun
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.

Everything you need to know about Oak Hill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oak Hill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oak Hill holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oak Hill holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oak Hill. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oak Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oak Hill holiday rentals we have selected for you start as low as £347 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oak Hill rentals

At Expedia, we put the best Oak Hill holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oak Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oak Hill holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oak Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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’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 Fowler Lake Park. 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.

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