A bridge over a calm river at sunset with a reflection of the sky and buildings.

Jefferson Holiday Rentals

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Our top choices for Jefferson holiday rentals

1. 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 NZ$571
includes taxes & fees
19 Oct - 20 Oct
3BR Home Near Hahns Lake – Newly Updated Kitchen

2. Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (52 reviews)
"Thank you for a peaceful stay, we came from Arizona to host my mothers memorial and the comfort and relaxation was well needed, plus it was big enough to have my kids spend time with us as well. Thank you for everything!"
United States
Kelly T.
The price is NZ$411
includes taxes & fees
13 Oct - 14 Oct
Log Cabin at Lake Koshkonong - “The Overlook”

3. Spacious Accessible Studio w/ Walk-In Shower

Spacious Accessible Studio w/ Walk-In Shower
Oconomowoc
The price is NZ$277
includes taxes & fees
1 Nov - 2 Nov
Spacious Accessible Studio w/ Walk-In Shower

4. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is NZ$477
includes taxes & fees
11 Oct - 12 Oct
Blue Lakeview Home

5. Vast Lake Koshkonong Views from Pier, Deck, & Home

Vast Lake Koshkonong Views from Pier, Deck, & Home
Edgerton
10.0 out of 10, Exceptional, (2 reviews)
The price is NZ$575
includes taxes & fees
26 Oct - 27 Oct
Vast Lake Koshkonong Views from Pier, Deck, & Home

6. 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 NZ$415
includes taxes & fees
8 Nov - 9 Nov
Historic Downtown Luxury-Lake-Coffee-Spa like BA

7. Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Edgerton
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful.. just beautiful and right at the hert if town"
United States
Georgia S.
The price is NZ$484
includes taxes & fees
8 Nov - 9 Nov
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

8. 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 NZ$605
includes taxes & fees
12 Oct - 13 Oct
Private Hot Tub • Bright Home Near Downtown

9. 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 NZ$725
includes taxes & fees
31 Oct - 1 Nov
Relax & Reboot in this Charming 2-Bedroom Townhome

10. 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.
Charming Historic Upper Walk to Downtown & Lakes

11. FirePit/Grill/PacMan Your Fall Escape Starts Here

FirePit/Grill/PacMan Your Fall Escape Starts Here
Milton
10.0 out of 10, Exceptional, (24 reviews)
"Clean, pet friendly and well appointed. Would be great to revisit in summer when we could enjoy all of the outdoor amenities. Highly recommend. "
United States
Vicky Z.
The price is NZ$1,202
includes taxes & fees
12 Oct - 13 Oct
FirePit/Grill/PacMan Your Fall Escape Starts Here

12. Edgewater Escape

Edgewater Escape
Milton
10.0 out of 10, Exceptional, (2 reviews)
"Peaceful & well-appointed. This quiet cabin on the lake served as ‘home base’ for a three day tour of southern Wisconsin. A perfect couples get-away for the two of us, it would have been just as well suited had we brought our two adult kids with separate rooms for each. Though among the smallest of the surrounding cabins, the floor plan was well-considered and spacious with a deck equally as spacious and while the dock was small, it still would have accommodated four of us in chairs or parking...
United States
Zane T.
The price is NZ$555
includes taxes & fees
21 Oct - 22 Oct
Edgewater Escape

13. 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 NZ$1,282
includes taxes & fees
14 Oct - 15 Oct
Sytlish Retreat Near Wedding Venues & Downtown

14. 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 NZ$551
includes taxes & fees
1 Nov - 2 Nov
Historic Downtown- King Bed-St Johns Acad-Shopping

15. Queen Studio Suite w/ Kitchenette in Oconomowoc

Queen Studio Suite w/ Kitchenette in Oconomowoc
Oconomowoc
The price is NZ$277
includes taxes & fees
18 Oct - 19 Oct
Queen Studio Suite w/ Kitchenette in Oconomowoc

16. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is NZ$812
includes taxes & fees
1 Nov - 2 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

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

Accessible 1-BR Queen Suite w/ Roll-In Shower
Oconomowoc
The price is NZ$321
includes taxes & fees
18 Oct - 19 Oct
Accessible 1-BR Queen Suite w/ Roll-In Shower

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

Accessible 1-BR Suite w/ Two Double Beds
Oconomowoc
The price is NZ$353
includes taxes & fees
2 Nov - 3 Nov
Accessible 1-BR Suite w/ Two Double Beds

19. 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 NZ$824
includes taxes & fees
14 Oct - 15 Oct
Dome House on Whitewater Lake

20. Accessible 1BR Suite | Pool & Daily Breakfast

Accessible 1BR Suite | Pool & Daily Breakfast
Oconomowoc
The price is NZ$353
includes taxes & fees
8 Nov - 9 Nov
Accessible 1BR Suite | Pool & Daily Breakfast
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 Jefferson Hotel Reviews

Find out more about Jefferson

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Jefferson holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Jefferson. 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 Jefferson. Seeing all the best attractions is bound to make you fall in love with Jefferson. Who knows, you may even be tempted to extend your 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 holiday 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 Jefferson short-term rentals, that won’t be hard to do.

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?

Adorable home w lake front- Paddle boats & kayaks ava, and 2 bathrooms!: 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 Glacial Drumlin State Trail West. 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.