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Oak Hill Vacation Rentals

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Our top choices for Oak Hill vacation rentals

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

Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast
Oconomowoc
10.0 out of 10, Exceptional, (1 review)
"."
United States
Rhonda M.
The price is CA $319
CA $410 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 2BR Suite w/ Pool, Hot Tub & Breakfast

2. Charming Historic Upper Walk to Downtown & Lakes

Charming Historic Upper Walk to Downtown & Lakes
Oconomowoc
10.0 out of 10, Exceptional, (42 reviews)
"Beautiful, comfortable house within easy walking distance of downtown and the beach. Thoughtful hosts with great communication. Thanks for a great return stay!"
United States
Mark G.
The price is CA $303
CA $768 total
includes taxes & fees
Oct 11 - Oct 12
Charming Historic Upper Walk to Downtown & Lakes

3. Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.6 out of 10, Exceptional, (10 reviews)
"Loved the location and it was just the perfect size for the two of us. Will definitely stay here again when we are in Delafield. "
United States
Becky M.
The price is CA $193
CA $339 total
includes taxes & fees
Oct 19 - Oct 20
Historic Downtown Luxury-Lake-Coffee-Spa like BA

4. Sytlish Retreat Near Wedding Venues & Downtown

Sytlish Retreat Near Wedding Venues & Downtown
Oconomowoc
10.0 out of 10, Exceptional, (30 reviews)
"Nicely remodeled home that was perfect for our trip to Oconomowoc"
United States
Carl G.
The price is CA $467
CA $984 total
includes taxes & fees
Oct 14 - Oct 15
Sytlish Retreat Near Wedding Venues & Downtown

5. Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.8 out of 10, Exceptional, (12 reviews)
"Comfortable, clean, convenient location and stylish decor. Owner was great! Will recommend to my friends."
United States
Susan D.
The price is CA $266
CA $450 total
includes taxes & fees
Oct 18 - Oct 19
Historic Downtown- King Bed-St Johns Acad-Shopping

6. 2-BR Suite w/ King & Double Beds + Kitchen

2-BR Suite w/ King & Double Beds + Kitchen
Oconomowoc
10.0 out of 10, Exceptional, (1 review)
"The two bedroom suite was perfect! The room was spotless and the furnishings were comfortable. They had breakfast and a social hour in the evening. It was very nice. We didn’t use the pool and it was great. Would definitely stay here again."
United States
Sharon J.
The price is CA $319
CA $410 total
includes taxes & fees
Nov 1 - Nov 2
2-BR Suite w/ King & Double Beds + Kitchen

7. 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)
"The house worked out just perfect for us! The surrounding grounds are beautiful also. A’Lisa was a very nice host and very easy to get into contact with. We will definitely be back!"
United States
Jon S.
The price is CA $441
CA $573 total
includes taxes & fees
Oct 11 - Oct 12
Relax & Reboot in this Charming 2-Bedroom Townhome

8. Accessible 2-BR Suite w/ Tub & 2 Bathrooms

Accessible 2-BR Suite w/ Tub & 2 Bathrooms
Oconomowoc
The price is CA $319
CA $392 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 2-BR Suite w/ Tub & 2 Bathrooms

9. Private Hot Tub • Bright Home Near Downtown

Private Hot Tub • Bright Home Near Downtown
Oconomowoc
10.0 out of 10, Exceptional, (6 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 $258
CA $487 total
includes taxes & fees
Oct 20 - Oct 21
Private Hot Tub • Bright Home Near Downtown

10. Accessible 1BR Suite | Pool & Daily Breakfast

Accessible 1BR Suite | Pool & Daily Breakfast
Oconomowoc
The price is CA $197
CA $255 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 1BR Suite | Pool & Daily Breakfast

11. Accessible 1-BR Queen Suite w/ Roll-In Shower

Accessible 1-BR Queen Suite w/ Roll-In Shower
Oconomowoc
The price is CA $197
CA $255 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 1-BR Queen Suite w/ Roll-In Shower

12. Accessible 1-BR Suite w/ Two Double Beds

Accessible 1-BR Suite w/ Two Double Beds
Oconomowoc
The price is CA $197
CA $255 total
includes taxes & fees
Nov 1 - Nov 2
Accessible 1-BR Suite w/ Two Double Beds

13. Dome House on Whitewater Lake

Dome House on Whitewater Lake
Whitewater
10.0 out of 10, Exceptional, (3 reviews)
"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 $263
CA $683 total
includes taxes & fees
Oct 14 - Oct 15
Dome House on Whitewater Lake

14. 3BR Home Near Hahns Lake – Newly Updated Kitchen

3BR Home Near Hahns Lake – Newly Updated Kitchen
Johnson Creek
10.0 out of 10, Exceptional, (1 review)
"House is great. Host was excellent when responding to any questions. FYI the bedrooms and bathroom were upstairs. Enjoy our time very much."
United States
D M.
The price is CA $215
CA $461 total
includes taxes & fees
Oct 19 - Oct 20
3BR Home Near Hahns Lake – Newly Updated Kitchen

15. Spacious Accessible Studio w/ Walk-In Shower

Spacious Accessible Studio w/ Walk-In Shower
Oconomowoc
The price is CA $167
CA $221 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Accessible Studio w/ Walk-In Shower

16. Queen Studio Suite w/ Kitchenette in Oconomowoc

Queen Studio Suite w/ Kitchenette in Oconomowoc
Oconomowoc
The price is CA $167
CA $221 total
includes taxes & fees
Nov 1 - Nov 2
Queen Studio Suite w/ Kitchenette in Oconomowoc

17. Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (8 reviews)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is CA $236
CA $412 total
includes taxes & fees
Oct 8 - Oct 9
Historic Downtown-Old World Charm-Dining-Coffee

18. 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, (31 reviews)
"The house was absolutely perfect!!! Thank you for a great relaxing weekend!"
United States
Annika V.
The price is CA $489
CA $1,120 total
includes taxes & fees
Oct 14 - Oct 15
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
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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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?

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle: This vacation home rental near Oak Hill is located on a lake and has an indoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 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.