Photo by Linda ❤

Jefferson Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Dec - 24 Dec
Tomorrow
24 Dec - 25 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Jefferson holiday rentals

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

Cottage in Milton

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute! Near winery and a supper club! "
United States
Juanita W.
The price is HK$735
HK$1,498 total
includes taxes & fees
24 Dec - 25 Dec
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
Property grounds
Log Cabin at Lake Koshkonong - “The Overlook”

Cabin in Edgerton

Log Cabin at Lake Koshkonong - “The Overlook”
9.2 out of 10, Wonderful, (48)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
The price is HK$700
HK$1,437 total
includes taxes & fees
24 Dec - 25 Dec
Log Cabin at Lake Koshkonong - “The Overlook”
Interior
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Condo in Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton
2.0 star property
10.0 out of 10, Exceptional, (5)
"Beautiful and interesting stay!! Comfortable and spacious accommodations for our visit to over the vines wedding venue.. "
United States
Amy S.
The price is HK$778
HK$1,978 total
includes taxes & fees
6 Jan - 7 Jan 2026
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Exterior
Historic Downtown Luxury-Lake-Coffee-Spa like BA

Apartment in Delafield

Historic Downtown Luxury-Lake-Coffee-Spa like BA
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 HK$988
HK$1,785 total
includes taxes & fees
2 Jan - 3 Jan 2026
Historic Downtown Luxury-Lake-Coffee-Spa like BA
Exterior
Pool. Gym. Near Aurora Medical Center!

Apartment in Oconomowoc

Pool. Gym. Near Aurora Medical Center!
The price is HK$771
HK$1,032 total
includes taxes & fees
4 Jan - 5 Jan 2026
Pool. Gym. Near Aurora Medical Center!
Fridge, microwave, oven, stovetop
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Holiday Home in Village of Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
10.0 out of 10, Exceptional, (7)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is HK$1,120
HK$3,524 total
includes taxes & fees
11 Jan - 12 Jan 2026
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Interior
HotTub/Kayaks/Arcade Your Dream Vacay Starts Here

Holiday Home in Milton

HotTub/Kayaks/Arcade Your Dream Vacay Starts Here
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.
HotTub/Kayaks/Arcade Your Dream Vacay Starts Here
Fridge, microwave, oven, stovetop
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.

Holiday Home in Oconomowoc

Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
2.0 star property
The price is HK$766
HK$1,797 total
includes taxes & fees
4 Jan - 5 Jan 2026
Bright, cozy 3BR ranch in Lake Country with fenced yard and covered patio.
Exterior
Free Breakfast, Gym, Great for Business Travelers!

Condo in Oconomowoc

Free Breakfast, Gym, Great for Business Travelers!
The price is HK$921
HK$1,198 total
includes taxes & fees
4 Jan - 5 Jan 2026
Free Breakfast, Gym, Great for Business Travelers!
Interior
Historic Downtown- King Bed-St Johns Acad-Shopping

Apartment in Delafield

Historic Downtown- King Bed-St Johns Acad-Shopping
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 HK$1,362
HK$2,365 total
includes taxes & fees
4 Jan - 5 Jan 2026
Historic Downtown- King Bed-St Johns Acad-Shopping
Exterior
comfortably sleeps 10 guests

Holiday Home in Elkhorn

comfortably sleeps 10 guests
10.0 out of 10, Exceptional, (41)
"Great place, great manager "
United States
Chris C.
The price is HK$1,167
HK$3,338 total
includes taxes & fees
19 Jan - 20 Jan 2026
comfortably sleeps 10 guests
Exterior
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨

Holiday Home in Oconomowoc

✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
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 HK$1,587
HK$3,763 total
includes taxes & fees
25 Dec - 26 Dec
✨ Stylish Home with Fire Pit: Near Downtown & Weddings Venues ✨
Property grounds
DElafield Rivers Gateway Luxurious Condo

Apartment in Delafield

DElafield Rivers Gateway Luxurious Condo
The price is HK$1,401
HK$4,256 total
includes taxes & fees
31 Dec - 1 Jan 2026
DElafield Rivers Gateway Luxurious Condo
Smart TV, fireplace, video games, DVD player
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-

Holiday Home in Elkhorn

Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
9.8 out of 10, Exceptional, (19)
"This was an awesome stay and would recommend!"
United States
Carson H.
The price is HK$2,816
HK$6,220 total
includes taxes & fees
8 Jan - 9 Jan 2026
Private 3br, with SwimSpa, Gym, by Hwy 43, 67 & 50-Alpine Valley, Ice Age Trail-
Exterior
Historic Downtown-Old World Charm-Dining-Coffee

Apartment in Delafield

Historic Downtown-Old World Charm-Dining-Coffee
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 HK$1,206
HK$2,163 total
includes taxes & fees
19 Jan - 20 Jan 2026
Historic Downtown-Old World Charm-Dining-Coffee
Exterior
Studio | Free Breakfast. Pool. Gym

Apartment in Oconomowoc

Studio | Free Breakfast. Pool. Gym
The price is HK$771
HK$1,032 total
includes taxes & fees
4 Jan - 5 Jan 2026
Studio | Free Breakfast. Pool. Gym
Exterior
Free Breakfast | Great for Business Travelers!

Condo in Oconomowoc

Free Breakfast | Great for Business Travelers!
The price is HK$1,520
HK$1,933 total
includes taxes & fees
30 Dec - 31 Dec
Free Breakfast | Great for Business Travelers!
Exterior
Free Breakfast. Suite Near Aurora Medical Center!

Condo in Oconomowoc

Free Breakfast. Suite Near Aurora Medical Center!
The price is HK$1,520
HK$1,933 total
includes taxes & fees
28 Dec - 29 Dec
Free Breakfast. Suite Near Aurora Medical Center!
Exterior
Pool. Gym. Your Next Trip!

Condo in Oconomowoc

Pool. Gym. Your Next Trip!
The price is HK$1,520
HK$1,933 total
includes taxes & fees
28 Dec - 29 Dec
Pool. Gym. Your Next Trip!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jefferson Hotel Reviews

Tru By Hilton Janesville

Tru By Hilton Janesville

10/10 Excellent
"Great everything, wish room was a bit more spacious since it was a kind bed but everything was great! "
Yesenia 1-night trip
Posted 18 hours ago
Tru By Hilton Janesville

Find out more about Jefferson

Search for holiday rentals in Jefferson on Expedia! You can easily find your home rentals, villas, holiday apartments in Jefferson using one of the methods below:

  • View our selection of featured holiday rentals in Jefferson
  • Use the map to find apartments and other holiday homes in the Jefferson neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jefferson while they last

Look no further and take a look at our great range of rental properties in Jefferson!

Frequently asked questions

Can I find a holiday rental in Jefferson?

Yes, there are holiday rentals in Jefferson close to Jefferson County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Jefferson is known for its festivals and cafés. Make sure you have time to check out the seafood restaurants and golf courses during your trip.

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

LAKEFRONT HIDDEN GEM !: This holiday home rental outside of Jefferson 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 can I see and do in Jefferson?

Enjoy the area's cultural attractions such as Hi-Way Outdoor Theatre, or get outdoors into nature at a spot like Lake Ripley Park Beach. While here, Jefferson County Fairgrounds and Jefferson Golf Club are other places worth a visit.

What are holiday rentals like in Jefferson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Jefferson. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment 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 an attractive option for a small group gathering.