A vast agricultural landscape with fields, roads, and scattered buildings under a clear sky.

Holiday Homes in Chilton

  • 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

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chilton holiday homes

Exterior detail

1. Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New Holstein
10.0 out of 10, Exceptional, (179 reviews)
"We stay there every year and are never disappointed. Great location and experience. Thank you!"
United States
Doug S.
The price is AU$452
includes taxes & fees
21 Sept - 22 Sept
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Property grounds

2. Lakefront Cottage on Lake Winnebago

Lakefront Cottage on Lake Winnebago
Hilbert
9.6 out of 10, Exceptional, (9 reviews)
"Liked the fire pits and the view "
United States
Mark M.
The price is AU$527
includes taxes & fees
13 Sept - 14 Sept
Lakefront Cottage on Lake Winnebago
Exterior

3. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (69 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is AU$381
includes taxes & fees
15 Sept - 16 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude
Exterior detail

4. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Reedsville
9.8 out of 10, Exceptional, (35 reviews)
"Our 4th time here. Great stay as always."
United States
Jason R.
The price is AU$660
includes taxes & fees
13 Sept - 14 Sept
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Interior

5. Centrally Located Home w/ Yard & Fast WiFi

Centrally Located Home w/ Yard & Fast WiFi
Oshkosh
10.0 out of 10, Exceptional, (6 reviews)
"Really comfortable place to stay, the kitchen is nice and we enjoyed a thunderstorm while sitting on the front porch"
United States
Peggy L.
Centrally Located Home w/ Yard & Fast WiFi
Interior

6. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Kiel
8.8 out of 10, Excellent, (6 reviews)
"This is an amazing and fun property. If you are in town for any event at Road America it makes it a little more special."
United States
Ryan K.
The price is AU$862
includes taxes & fees
11 Sept - 12 Sept
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Exterior

7. Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly

Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Oshkosh
9.6 out of 10, Exceptional, (35 reviews)
"Very nice stay, well accommodating."
United States
Chris S.
The price is AU$514
includes taxes & fees
17 Sept - 18 Sept
Waterfront Retreat on Lake Winnebago, Kayaks, Firepit, Dog Friendly
Iron/ironing board, WiFi, bed sheets

8. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AU$253
includes taxes & fees
19 Sept - 20 Sept
Victorian Inn #241 | 2 Queen Beds
TV, offices

9. Waterfront House w/ Patio Near Riverside Park

Waterfront House w/ Patio Near Riverside Park
Kaukauna
10.0 out of 10, Exceptional, (1 review)
"Great stay and location."
United States
Cody W.
Waterfront House w/ Patio Near Riverside Park
Terrace/patio

10. Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago

Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
Oshkosh
9.6 out of 10, Exceptional, (4 reviews)
"This was the perfect short-notice getaway for us. Pet friendly, extra quiet neighborhood, close to everything. Check in was a breeze, the place was clean. I am verry happy with our stay."
United States
Charles W.
The price is AU$495
includes taxes & fees
15 Sept - 16 Sept
Cozy 2BR • Firepit • Minutes to Downtown & UW Campus • Near Lake Winnebago
TV, fireplace, offices

11. Riverfront Retreat w/ Fireplace & Fast WiFi

Riverfront Retreat w/ Fireplace & Fast WiFi
Appleton
6.8 out of 10, (3 reviews)
"The house was lovely. "
United States
MaryAnne G.
Riverfront Retreat w/ Fireplace & Fast WiFi
Coffee/tea maker, fridge, microwave, stovetop

12. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
Updated Plymouth Home ~ 5 Mi to Road America!
Interior

13. Historic City Park home within walking distance to all downtown has to offer!

Historic City Park home within walking distance to all downtown has to offer!
Appleton
9.8 out of 10, Exceptional, (19 reviews)
"The throwback vibes in this house were wonderful. Very clean and close enough to College Avenue that we didn’t drive anywhere once we got to the house. We were able to walk everywhere we wanted to. Overall it was a great experience!"
United States
Jeff U.
The price is AU$322
includes taxes & fees
14 Sept - 15 Sept
Historic City Park home within walking distance to all downtown has to offer!
Exterior detail

14. Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago

Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
Oshkosh
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time staying herePlenty of room to hang out inAnd for us it easily slept 4 adults Location was close to grocerys / resteraunts etc ."
United States
Michael B.
The price is AU$516
includes taxes & fees
8 Oct - 9 Oct
Lake Channel 'Brewhaus' Townhouse: 2 bedrooms with 6 levels on Lake Winnebago
Living area

15. Oshkosh's #1 Home Away From Home

Oshkosh's #1 Home Away From Home
Oshkosh
The price is AU$497
includes taxes & fees
23 Sept - 24 Sept
Oshkosh's #1 Home Away From Home
Private kitchen

16. Cozy 1-bedroom house w/ Washer and dryer available

Cozy 1-bedroom house w/ Washer and dryer available
Fond du Lac
8.8 out of 10, Excellent, (3 reviews)
"Priced high due to EAA week. Only about 20 minutes from Oshkosh. Very clean."
United States
Leslie W.
The price is AU$321
includes taxes & fees
1 Oct - 2 Oct
Cozy 1-bedroom house w/ Washer and dryer available
Dining

17. Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs

Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
Menasha
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay. Peaceful and clean."
United States
Josh W.
The price is AU$849
includes taxes & fees
15 Sept - 16 Sept
Lux Designer Lakefront Home with Views, Firepit, Dock, Kayaks, and up to 2 Dogs
Coffee/tea maker, fridge, microwave, oven

18. Cozy Retreat • Fireplace Loft •Walk to Park & Lake

Cozy Retreat • Fireplace Loft •Walk to Park & Lake
Oshkosh
9.6 out of 10, Exceptional, (14 reviews)
"Was a great place for our Oshkosh fly in stay! "
United States
William N.
The price is AU$521
includes taxes & fees
13 Sept - 14 Sept
Cozy Retreat • Fireplace Loft •Walk to Park & Lake
Smart TV, DVD player, video library

19. Steps from Downtown

Steps from Downtown
Appleton
9.8 out of 10, Exceptional, (64 reviews)
"We loved staying in this beautiful and comfortable home! Our hosts thought of everything we might need and were very responsive when we had a question. We would highly recommend renting this property!"
United States
Michelle G.
The price is AU$539
includes taxes & fees
29 Sept - 30 Sept
Steps from Downtown
4 bedrooms, desk, iron/ironing board, travel cot

20. 2 Min to Downtown Appleton! 4BD/2BA

2 Min to Downtown Appleton! 4BD/2BA
Appleton
9.8 out of 10, Exceptional, (35 reviews)
"Nice location to lots of sites. Good communications. Fewer check-out requirements compared to other properties. We'd stay again. "
United States
Ross S.
The price is AU$620
includes taxes & fees
16 Sept - 17 Sept
2 Min to Downtown Appleton! 4BD/2BA
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 Chilton Hotel Reviews

Baymont by Wyndham Appleton

Baymont by Wyndham Appleton

8/10 Good
"Bathroom door wouldn’t close and ac unit too loud. Ok if you just want a place to sleep and cheaper"
Tou 1-night trip
Posted 2 hours ago
Baymont by Wyndham Appleton

Find out more about Chilton

Chilton Holiday Homes information

Number of reviews
538
Accommodation
480 Holiday Homes
Lowest Price
AU$253
Highest Price
AU$862