Hebron Holiday Rentals

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Our top choices for Hebron holiday rentals

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
2.0 star property
Milton
9.6 out of 10, Exceptional, (5)
"Cute! Near winery and a supper club! "
United States
Juanita W.
The price is AU$236
includes taxes & fees
14 Dec - 15 Dec
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Studio | Free Breakfast. Pool. Gym

Studio | Free Breakfast. Pool. Gym
Oconomowoc
Studio | Free Breakfast. Pool. Gym

Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (48)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
The price is AU$257
includes taxes & fees
17 Dec - 18 Dec
Log Cabin at Lake Koshkonong - “The Overlook”

comfortably sleeps 10 guests

comfortably sleeps 10 guests
Elkhorn
10.0 out of 10, Exceptional, (40)
"Great property for our week in Elkhorn! Will definitely book again."
United States
Jon B.
The price is AU$648
includes taxes & fees
18 Dec - 19 Dec
comfortably sleeps 10 guests

Historic Downtown Luxury-Lake-Coffee-Spa like BA

Historic Downtown Luxury-Lake-Coffee-Spa like BA
Delafield
9.4 out of 10, Exceptional, (6)
"We were in town for a wedding and this place was perfect. Great location, close to restaurants, shopping and the wedding venue was only 15 minutes away. Unit was very clean and comfortable. It had everything we needed. We loved Angelina's Restaurant which is right around the corner. If you stay here definitely eat at Angelina's."
United States
Christopher M.
The price is AU$349
includes taxes & fees
14 Dec - 15 Dec
Historic Downtown Luxury-Lake-Coffee-Spa like BA

Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.6 out of 10, Exceptional, (4)
"Clean place. "
United States
John M.
The price is AU$389
includes taxes & fees
29 Dec - 30 Dec
Relax & Reboot in this Charming 2-Bedroom Townhome

Arcade/Fireplace/CoffeeBar The Holidays Start Here

Arcade/Fireplace/CoffeeBar The Holidays Start Here
Milton
10.0 out of 10, Exceptional, (17)
"We had the best VRBO experience at Harbor House. The hosts are absolutely fabulous. The house was perfect, just as presented online. 6 of us adults and a little French bulldog spent a long weekend there so we could cheer on our son (one of the visitors) as he ran the half Ironman in Madison. He LOVED the hot tub afterward. Great visit. Would definitely stay again if in the area."
United States
Karrie S.
The price is AU$813
includes taxes & fees
15 Dec - 16 Dec
Arcade/Fireplace/CoffeeBar The Holidays Start Here

Historic Downtown- King Bed-St Johns Acad-Shopping

Historic Downtown- King Bed-St Johns Acad-Shopping
Delafield
9.4 out of 10, Exceptional, (6)
"Needed a low cost option for staying downtown for a business meeting. Super convenient and very nice."
United States
Eric B.
The price is AU$461
includes taxes & fees
14 Dec - 15 Dec
Historic Downtown- King Bed-St Johns Acad-Shopping

Free Breakfast, Gym, Great for Business Travelers!

Free Breakfast, Gym, Great for Business Travelers!
Oconomowoc
The price is AU$232
includes taxes & fees
22 Dec - 23 Dec
Free Breakfast, Gym, Great for Business Travelers!

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Oconomowoc
10.0 out of 10, Exceptional, (19)
"Clean, cozy and convenient for walks dowtown! Stayed a week- Loved all of the special touches- including lots of towels, keurig pods and the smores basket! Thank you for a liovely stay in Oconomowoc."
United States
sk k.
The price is AU$739
includes taxes & fees
29 Dec - 30 Dec
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

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
9.8 out of 10, Exceptional, (19)
"This was an awesome stay and would recommend!"
United States
Carson H.
The price is AU$1,156
includes taxes & fees
22 Dec - 23 Dec
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

DElafield Rivers Gateway Luxurious Condo

DElafield Rivers Gateway Luxurious Condo
Delafield
The price is AU$872
includes taxes & fees
31 Dec - 1 Jan 2026
DElafield Rivers Gateway Luxurious Condo

Pool. Gym. Near Aurora Medical Center!

Pool. Gym. Near Aurora Medical Center!
Oconomowoc
Pool. Gym. Near Aurora Medical Center!

Waterfront - Hot Tub - Sauna - Game Room - Pets

Waterfront - Hot Tub - Sauna - Game Room - Pets
Edgerton
8.8 out of 10, Excellent, (5)
"Overall a really great place! Lots of space to spread out in the house and lots of fun stuff providing with the paddle boards, kayaks, and games. The back deck is huge, but could use a good cleaning. I would recommend this place. "
United States
Jessica D.
The price is AU$1,063
includes taxes & fees
16 Dec - 17 Dec
Waterfront - Hot Tub - Sauna - Game Room - Pets

Historic Downtown-Old World Charm-Dining-Coffee

Historic Downtown-Old World Charm-Dining-Coffee
Delafield
10.0 out of 10, Exceptional, (5)
"Great place to rest and relax on a fun weekend getaway. "
United States
Jeffrey C.
The price is AU$422
includes taxes & fees
14 Dec - 15 Dec
Historic Downtown-Old World Charm-Dining-Coffee

Free Breakfast. Suite Near Aurora Medical Center!

Free Breakfast. Suite Near Aurora Medical Center!
Oconomowoc
The price is AU$374
includes taxes & fees
18 Dec - 19 Dec
Free Breakfast. Suite Near Aurora Medical Center!

Pool. Gym. Your Next Trip!

Pool. Gym. Your Next Trip!
Oconomowoc
The price is AU$372
includes taxes & fees
12 Jan - 13 Jan 2026
Pool. Gym. Your Next Trip!

Free Breakfast | Great for Business Travelers!

Free Breakfast | Great for Business Travelers!
Oconomowoc
The price is AU$366
includes taxes & fees
21 Dec - 22 Dec
Free Breakfast | Great for Business Travelers!

Free Breakfast, Pool, Hot Tub, Gym. Great Suite!

Free Breakfast, Pool, Hot Tub, Gym. Great Suite!
Oconomowoc
4.0 out of 10, (1)
The price is AU$275
includes taxes & fees
18 Dec - 19 Dec
Free Breakfast, Pool, Hot Tub, Gym. Great Suite!
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 Hebron Hotel Reviews

Find out more about Hebron

Everything you need to know about Hebron 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 Hebron holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Hebron holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hebron holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hebron. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hebron 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 Hebron holiday rentals we have selected for you start as low as AU$236 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hebron rentals

At Expedia, we put the best Hebron 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 Hebron 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 Hebron 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 Hebron. 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 Hebron?

Yes, there are holiday rentals close to the most popular sights in Hebron, 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 Hebron has to offer?

LAKEFRONT HIDDEN GEM !: This holiday home rental outside of Hebron is located on the beach, and has a fireplace, a patio 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Hebron?

While exploring the area, visit family-friendly sights like Kettle Moraine Ranch, or get outside and enjoy nature at Lake Koshkonong. In the wider area, you’ll find University of Wisconsin-Whitewater and Cravath Lakefront Park.

What’s a holiday rental in Hebron like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hebron. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a family getaway.